(4R)-1-[(Benzyloxy)carbonyl]-4-hydroxy-L-proline

Basic Information

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CAS Number

13504-85-3

Molecular Formula

C13H15NO5

Molecular Weight

265.27 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Ethers

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

104-107 °C

Boiling Point

486.9°C at 760 mmHg

Density

1.4160

Water Solubility

Slightly soluble in water.

Flash Point

248.3℃

Refractive Index

1.612

Specific Rotation

-44 ° ~ -54 ° (c=2%, in C2H5OH)

SMILES

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O[C@@H]1C[C@H](N(C1)C(=O)OCc2ccccc2)C(=O)O

InChI

InChI=1S/C13H15NO5/c15-10-6-11(12(16)17)14(7-10)13(18)19-8-9-4-2-1-3-5-9/h1-5,10-11,15H,6-8H2,(H,16,17)/t10-,11+/m1/s1

InChIKey

WWVCWLBEARZMAH-MNOVXSKESA-N

LogP

0.8430000000000002

Topological Polar Surface Area

87.07000000000001 Å²

Hydrogen Bond Donor/Acceptor

2 / 6

Complexity

340

Safety Information

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Hazard Statement

H302 Harmful if swallowed
Acute toxicity, oral

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H332 Harmful if inhaled
Acute toxicity, inhalation

H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Synonyms & References

English

Z-L-4-hydroxyproline
N-Z-4-hydroxy-L-proline (trans)
N-cbz-hydroxy-L-proline
Z-L-Hyp-OH
N-Carbobenzyloxy-4-hydroxy-L-proline (trans)
Cbz-Hyp-OH
z-Hydroxyproline
Z-Hyp-OH
trans-N-Carbobenzoxy-4-hydroxy-L-proline
(2S,4R)-4-Hydroxy-1,2-pyrrolidinedicarboxylic Acid 1-Benzyl Ester
Benzyloxycarbonyl-L-4-hydroxyproline
H-His(Trt)-OH
Z-O-Hyp-OH
CBZ-L-HYDROXYPROLINE
CBZ-L-HYP-OH
N-Cbz-Hydroxy-L-prol
N-Cbz-trans-4-hydroxy-L-proline
trans-N-Cbz-4-hydroxy-L-proline
Z-L-HYDROXYPROLINE
Z-trans-4-hydroxy-L-proline
trans-N-Benzyloxycarbonyl-4-hydroxy-L-proline
N-Benzyloxycarbonyl-L-Hydroproline
Z-HYP(BZL)-OH
(2S,4R)-1-[(benzyloxy)carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid

MDL Number

MFCD00037329

FAQ

What are the physical and chemical properties of (4R)-1-[(Benzyloxy)carbonyl]-4-hydroxy-L-proline (CAS: 13504-85-3)?

(4R)-1-[(Benzyloxy)carbonyl]-4-hydroxy-L-proline is a white crystalline solid. Its molecular weight is approximately 300.36 g/mol. It is poorly water-soluble but soluble in organic solvents. This compound exhibits moderate reactivity, particularly towards nucleophilic attack at the hydroxyl group.

How is (4R)-1-[(Benzyloxy)carbonyl]-4-hydroxy-L-proline (CAS: 13504-85-3) typically synthesized?

(4R)-1-[(Benzyloxy)carbonyl]-4-hydroxy-L-proline is synthesized by the condensation of benzyloxycarbonyl chloride with (4R)-4-hydroxy-L-proline. This reaction is catalyzed by triethylamine in dichloromethane. The product is purified by column chromatography, yielding a high yield of 80-85%.

What industries use (4R)-1-[(Benzyloxy)carbonyl]-4-hydroxy-L-proline (CAS: 13504-85-3)?

(4R)-1-[(Benzyloxy)carbonyl]-4-hydroxy-L-proline is primarily used in pharmaceuticals for the synthesis of biologically active compounds. It also finds applications in the production of polymers and as a precursor in the development of new materials for sensors and semiconductors.

What precautions should be taken when handling (4R)-1-[(Benzyloxy)carbonyl]-4-hydroxy-L-proline (CAS: 13504-85-3)?

Proper personal protective equipment (PPE) such as gloves, goggles, and a lab coat should be worn when handling (4R)-1-[(Benzyloxy)carbonyl]-4-hydroxy-L-proline. It should be stored in a cool, dry place, away from direct sunlight and sources of heat. In case of spill, it should be cleaned up using appropriate procedures and materials. Always refer to the Material Safety Data Sheet (MSDS) for detailed safety information.