(S)-1-Cbz-2-pyrrolidineacetic acid

Base Information

• Chemical Name: (S)-1-Cbz-2-pyrrolidineacetic acid
• CAS No.: 56633-73-9
• Molecular Formula: C14H17NO4
• Molecular Weight: 263.293
• DSSTox Substance ID: DTXSID00446545
• Mol file: 56633-73-9.mol

Synonyms:(S)-1-Cbz-2-pyrrolidineacetic acid;56633-73-9;2-[(2S)-1-phenylmethoxycarbonylpyrrolidin-2-yl]acetic Acid;(S)-2-(1-((Benzyloxy)carbonyl)pyrrolidin-2-yl)acetic acid;2-[(2S)-1-[(benzyloxy)carbonyl]pyrrolidin-2-yl]acetic acid;SCHEMBL1122258;(S)-2-(1-(benzyloxycarbonyl)pyrrolidin-2-yl)acetic acid;DTXSID00446545;VNCNCAUMHGXGGZ-LBPRGKRZSA-N;EN300-6253693;{(2S)-1-[(Benzyloxy)carbonyl]pyrrolidin-2-yl}acetic acid;(S)-2-carboxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property of (S)-1-Cbz-2-pyrrolidineacetic acid

Chemical Property:

• Melting Point: 73-75 °C
• Boiling Point: 448.4±28.0 °C(Predicted)
• PKA: 4.56±0.10(Predicted)
• PSA: 66.84000
• Density: 1.252±0.06 g/cm3(Predicted)
• LogP: 2.20020
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 263.11575802
• Heavy Atom Count: 19
• Complexity: 325

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)OCC2=CC=CC=C2)CC(=O)O
• Isomeric SMILES: C1C[C@H](N(C1)C(=O)OCC2=CC=CC=C2)CC(=O)O

Technology Process of (S)-1-Cbz-2-pyrrolidineacetic acid

There total 7 articles about (S)-1-Cbz-2-pyrrolidineacetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 66.0%

benzyl chloroformate (501-53-1,94274-21-2) + 2-[(2S)-pyrrolidin-2-yl]acetic acid hydrochloride (439918-59-9,53912-85-9) → (S)-2-(1-((benzyloxy)carbonyl)pyrrolidine-2-yl)acetic acid (56633-73-9)

Guidance literature:

benzyl chloroformate; 2-[(2S)-pyrrolidin-2-yl]acetic acid hydrochloride; With sodium hydroxide; In water; at 0 ℃; for 2h;

With hydrogenchloride; In water; pH=3;

Reference yield: 62.0%

benzyl (S)-1-benzyloxycarbonylpirrolidine-2-acetate (77100-95-9) → (S)-2-(1-((benzyloxy)carbonyl)pyrrolidine-2-yl)acetic acid (56633-73-9)

Guidance literature:

With potassium carbonate; In methanol; water; for 6h; Heating;

DOI:10.1248/cpb.29.3249

Reference yield:

N-Benzyloxycarbonyl-L-proline (1148-11-4) → (S)-2-(1-((benzyloxy)carbonyl)pyrrolidine-2-yl)acetic acid (56633-73-9)

Guidance literature:

Multi-step reaction with 2 steps

1: ClCOOEt; N-methylmorpholine

2: CF₃COOAg / dioxane; H₂O / sonication

With 4-methyl-morpholine; silver trifluoroacetate; chloroformic acid ethyl ester; In 1,4-dioxane; water; 2: Wolff rearrangement;

DOI:10.1002/hlca.200690235

upstream raw materials:

benzyl (S)-1-benzyloxycarbonylpirrolidine-2-acetate

(-)-(S)-2-methoxycarbonylmethylpyrrolidine-1-carboxylic acid benzyl ester

2-(S)-(2-diazo-1-oxoethyl)pyrrolidine-1-carboxylic acid benzyl ester

N-Benzyloxycarbonyl-L-proline

Downstream raw materials:

N-Cbz-β-HProN(Me)PheNH2

(-)-(S)-2-(2-hydroxyethyl)pyrrolidine-1-carboxylic acid benzyl ester

(+)-coniceine

(S)-hexahydroindolizin-5(1H)-one