(S)-1-{2-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-tert-butoxy-propionylamino)-3-methyl-butyrylamino]-2-methyl-propionyl}-pyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (S)-1-{2-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-tert-butoxy-propionylamino)-3-methyl-butyrylamino]-2-methyl-propionyl}-pyrrolidine-2-carboxylic acid
• CAS No.: 177747-28-3
• Molecular Formula: C₂₉H₄₄N₄O₈
• Molecular Weight: 576.69
• Mol file: 177747-28-3.mol

Synonyms:(S)-1-{2-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-tert-butoxy-propionylamino)-3-methyl-butyrylamino]-2-methyl-propionyl}-pyrrolidine-2-carboxylic acid

Chemical Property of (S)-1-{2-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-tert-butoxy-propionylamino)-3-methyl-butyrylamino]-2-methyl-propionyl}-pyrrolidine-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-{2-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-tert-butoxy-propionylamino)-3-methyl-butyrylamino]-2-methyl-propionyl}-pyrrolidine-2-carboxylic acid

There total 10 articles about (S)-1-{2-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-tert-butoxy-propionylamino)-3-methyl-butyrylamino]-2-methyl-propionyl}-pyrrolidine-2-carboxylic 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: 68.0%

(S)-1-{2-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-tert-butoxy-propionylamino)-3-methyl-butyrylamino]-2-methyl-propionyl}-pyrrolidine-2-carboxylic acid methyl ester (177747-27-2) → (S)-1-{2-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-tert-butoxy-propionylamino)-3-methyl-butyrylamino]-2-methyl-propionyl}-pyrrolidine-2-carboxylic acid (177747-28-3)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; Ambient temperature;

DOI:10.1002/hlca.19960790220

Reference yield:

(S)-methyl 1-(isobutyryl)pyrrolidine-2-carboxylate (177747-23-8) → (S)-1-{2-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-tert-butoxy-propionylamino)-3-methyl-butyrylamino]-2-methyl-propionyl}-pyrrolidine-2-carboxylic acid (177747-28-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) COCl₂; 2.) 1,4-diazabicyclo<2.2.2>octane / 1.) CH₂Cl₂, DMF, r.t., 3.5 d; 2.) CH₂Cl₂, 0 deg C, 1 h

2: 52 percent / NaN₃ / tetrahydrofuran

3: 66 percent / CH₂Cl₂ / 18 h / Ambient temperature

4: 68 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / Ambient temperature

With 1,4-diaza-bicyclo[2.2.2]octane; lithium hydroxide; sodium azide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1002/hlca.19960790220

Reference yield:

L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → (S)-1-{2-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-tert-butoxy-propionylamino)-3-methyl-butyrylamino]-2-methyl-propionyl}-pyrrolidine-2-carboxylic acid (177747-28-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) SOCl₂; 2.) Et₃N / 1.) reflux, 1 h; 2.) AcOEt, r.t., overnight

2: 1.) COCl₂; 2.) 1,4-diazabicyclo<2.2.2>octane / 1.) CH₂Cl₂, DMF, r.t., 3.5 d; 2.) CH₂Cl₂, 0 deg C, 1 h

3: 52 percent / NaN₃ / tetrahydrofuran

4: 66 percent / CH₂Cl₂ / 18 h / Ambient temperature

5: 68 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / Ambient temperature

With 1,4-diaza-bicyclo[2.2.2]octane; lithium hydroxide; thionyl chloride; sodium azide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1002/hlca.19960790220

upstream raw materials:

(S)-1-{2-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-tert-butoxy-propionylamino)-3-methyl-butyrylamino]-2-methyl-propionyl}-pyrrolidine-2-carboxylic acid methyl ester

N-benzyloxycarbonyl-O-t-butyl-L-serine

L-valine methylester hydrochloride

Z-Ser(Bu^t)-Val-OH

Downstream raw materials:

Z-Ser(t-Bu)-Val-Aib-Pro-Aib-Leu-Aib-Pro-Leuol

2-[((S)-1-{2-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-tert-butoxy-propionylamino)-3-methyl-butyrylamino]-2-methyl-propionyl}-pyrrolidine-2-carbonyl)-amino]-2-methyl-propionic acid

{(S)-2-tert-Butoxy-1-[(S)-1-(1,1-dimethyl-2-{(S)-2-[1-methyl-1-(methyl-phenyl-carbamoyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethylcarbamoyl)-2-methyl-propylcarbamoyl]-ethyl}-carbamic acid benzyl ester