(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Basic Information

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CAS Number

61-33-6

Molecular Formula

C16H18N2O4S

Molecular Weight

334.4 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Basic Physical Properties

Melting Point

214-217 °C

Boiling Point

663.3°C at 760 mmHg

Density

1.2729 (rough estimate)

Flash Point

355°C

Solubility

H2O: 100 mg/mL

Refractive Index

1.6930 (estimate)

Specific Rotation

D +282° (ethanol)

SMILES

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CC1(C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CC=C3)C(=O)O)C

InChI

InChI=1S/C16H18N2O4S/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1

InChIKey

JGSARLDLIJGVTE-MBNYWOFBSA-N

LogP

0.8607999999999998

Topological Polar Surface Area

86.71000000000001 Å²

Hydrogen Bond Donor/Acceptor

2 / 6

Complexity

530

Synonyms & References

English

DTXCID3026934
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6- (2-phenylacetamido)-
61-33-6
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- (2S,5R,6R)-
MLS001173382
HY-N7139
Free benzylpenicillin
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- [2S-(2.alpha.,5.alpha.,6.beta.)]-
penicillin g
Pfizerpen
NSC 131815
Penicillin
PHENOXYMETHYLPENICILLIN (BENZATHINE) TETRAHYDRATE IMPURITY A [EP IMPURITY]
(2S,5R,6R)-3,3-DIMETHYL-7-OXO-6-[(PHENYLACETYL)AMINO]-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID
NINDS_000316
IDI1_000316
AKOS005203091
PENICILLIN G [HSDB]
Bicillin (*Benzathine Salt, Tetrahydrate*)
PENICILLIN G [MI]
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid
Benzylpenicillin G
KBio2_001413
EINECS 204-038-0
PENICILLIN-G
GTPL4796
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Pencillin G
KBio2_006549
CHEBI:18208

MDL Number

MFCD00069665

Customs Code

32041900

FAQ

What are the physical and chemical properties of (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (CAS: 61-33-6)?

(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid is a crystalline solid with a molecular weight of approximately 305.27 g/mol. It has limited water solubility and high reactivity due to its carboxylic acid and amino functionalities. This compound is typically stored in a dry, cool place to prevent hydrolysis and is known for its ability to form salts and esters easily.

How is (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (CAS: 61-33-6) typically synthesized?

(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid can be synthesized through the condensation of (phenylacetyl)amine with 6,7-dimethyl-3-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid. The reaction is typically catalyzed by a strong base like sodium hydride to promote the nucleophilic attack, yielding a high isolated yield of about 85%. The process requires careful handling and is usually performed under an inert atmosphere to prevent decomposition.

What industries use (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (CAS: 61-33-6)?

(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid finds application in pharmaceuticals, where it serves as an intermediate in the synthesis of various bioactive compounds. It is also used in the development of new polymer materials and as a sensor component in certain analytical devices. This compound's unique structure and reactivity make it valuable in diverse fields requiring specialized chemical reagents.

What precautions should be taken when handling (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (CAS: 61-33-6)?

When handling (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, it is essential to wear appropriate personal protective equipment (PPE) including gloves, goggles, and a lab coat. Use a fume hood to avoid inhalation of any vapors. Spills should be cleaned up immediately using absorbent materials and proper containment. Always consult the Safety Data Sheet (SDS) for detailed handling instructions and emergency procedures.