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

Base Information

• Chemical Name: 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
• CAS No.: 177747-30-7
• Molecular Formula: C₃₃H₅₁N₅O₉
• Molecular Weight: 661.796
• Mol file: 177747-30-7.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 12 articles about 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 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: 91.0%

{(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 (177747-29-4) → 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 (177747-30-7)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 0 ℃; for 2.5h;

DOI:10.1002/hlca.19960790220

Reference yield:

(S)-methyl 1-(isobutyryl)pyrrolidine-2-carboxylate (177747-23-8) → 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 (177747-30-7)

Guidance literature:

Multi-step reaction with 6 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

5: 42 percent / CH₂Cl₂

6: 91 percent / 6N aq. HCl / tetrahydrofuran / 2.5 h / 0 °C

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; 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) → 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 (177747-30-7)

Guidance literature:

Multi-step reaction with 7 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

6: 42 percent / CH₂Cl₂

7: 91 percent / 6N aq. HCl / tetrahydrofuran / 2.5 h / 0 °C

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

DOI:10.1002/hlca.19960790220

upstream raw materials:

{(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

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