(S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid; compound with (2S,3aS,6aS)-octahydro-cyclopenta[b]pyrrole-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid; compound with (2S,3aS,6aS)-octahydro-cyclopenta[b]pyrrole-2-carboxylic acid benzyl ester
• CAS No.: 93779-32-9
• Molecular Formula: C₁₅H₁₉NO₂*C₁₇H₁₇NO₄
• Molecular Weight: 544.648
• Mol file: 93779-32-9.mol

Synonyms:(S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid; compound with (2S,3aS,6aS)-octahydro-cyclopenta[b]pyrrole-2-carboxylic acid benzyl ester

Chemical Property of (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid; compound with (2S,3aS,6aS)-octahydro-cyclopenta[b]pyrrole-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid; compound with (2S,3aS,6aS)-octahydro-cyclopenta[b]pyrrole-2-carboxylic acid benzyl ester

There total 5 articles about (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid; compound with (2S,3aS,6aS)-octahydro-cyclopenta[b]pyrrole-2-carboxylic acid benzyl ester 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:

N-Cbz-L-Phe (1161-13-3) + cis,endo-2-azabicyclo<3.3.0>octane-3-carboxylic acid benzylester hydrochloride (87269-87-2,87679-25-2,88547-79-9,93779-29-4,94569-19-4,138877-09-5) → (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid; compound with (2S,3aS,6aS)-octahydro-cyclopenta[b]pyrrole-2-carboxylic acid benzyl ester (93779-32-9)

Guidance literature:

With sodium hydroxide; Yield given. Multistep reaction; 1.) methylene chloride; 2.) ethylacetate, cyclohexane;

DOI:10.1016/S0040-4039(01)81471-4

Reference yield:

1-pyrrolidinocyclopent-1-ene (7148-07-4) → (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid; compound with (2S,3aS,6aS)-octahydro-cyclopenta[b]pyrrole-2-carboxylic acid benzyl ester (93779-32-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 290 g / triethylamine / dimethylformamide / 24 h / Ambient temperature

2: 2N HCl / 1 h / Heating

3: H₂ / Pd/C / acetic acid / 3750.3 Torr

4: 91 percent / SOCl₂ / 15 h / Ambient temperature

5: 1.) 10percent NaOH / 1.) methylene chloride; 2.) ethylacetate, cyclohexane

With hydrogenchloride; sodium hydroxide; thionyl chloride; hydrogen; triethylamine; palladium on activated charcoal; In acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)81471-4

Reference yield:

(±)-methyl 2-(acetylamino)-3-(2-oxocyclopentyl)-propionate (87269-85-0) → (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid; compound with (2S,3aS,6aS)-octahydro-cyclopenta[b]pyrrole-2-carboxylic acid benzyl ester (93779-32-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 2N HCl / 1 h / Heating

2: H₂ / Pd/C / acetic acid / 3750.3 Torr

3: 91 percent / SOCl₂ / 15 h / Ambient temperature

4: 1.) 10percent NaOH / 1.) methylene chloride; 2.) ethylacetate, cyclohexane

With hydrogenchloride; sodium hydroxide; thionyl chloride; hydrogen; palladium on activated charcoal; In acetic acid;

DOI:10.1016/S0040-4039(01)81471-4

upstream raw materials:

N-Cbz-L-Phe

cis,endo-2-azabicyclo<3.3.0>octane-3-carboxylic acid benzylester hydrochloride

1-pyrrolidinocyclopent-1-ene

(±)-methyl 2-(acetylamino)-3-(2-oxocyclopentyl)-propionate

Downstream raw materials:

benzyl (2S,3AS,6AS)-octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride

Refernces