tert-butyl (2S,4S)-1-(tert-butoxycarbonyl)-4-(cyanomethyl)pyroglutamate

Base Information

• Chemical Name: tert-butyl (2S,4S)-1-(tert-butoxycarbonyl)-4-(cyanomethyl)pyroglutamate
• CAS No.: 153080-73-0
• Molecular Formula: C₁₆H₂₄N₂O₅
• Molecular Weight: 324.377
• Mol file: 153080-73-0.mol

Synonyms:tert-butyl (2S,4S)-1-(tert-butoxycarbonyl)-4-(cyanomethyl)pyroglutamate

Chemical Property of tert-butyl (2S,4S)-1-(tert-butoxycarbonyl)-4-(cyanomethyl)pyroglutamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2S,4S)-1-(tert-butoxycarbonyl)-4-(cyanomethyl)pyroglutamate

There total 1 articles about tert-butyl (2S,4S)-1-(tert-butoxycarbonyl)-4-(cyanomethyl)pyroglutamate 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: 49.0%

iodoacetonitrile (624-75-9) + tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate (91229-91-3) → tert-butyl (2S,4S)-1-(tert-butoxycarbonyl)-4-(cyanomethyl)pyroglutamate (153080-73-0) + tert-butyl (2S,4R)-1-(tert-butoxycarbonyl)-4-(cyanomethyl)pyroglutamate (153080-74-1)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; Product distribution; 1.) 1 h, 2.) 2 h;

DOI:10.1016/S0040-4020(01)96272-6

Reference yield:

tert-butyl (2S,4S)-1-(tert-butoxycarbonyl)-4-(cyanomethyl)pyroglutamate (153080-73-0) → (S)-3-((S)-2-Amino-2-tert-butoxycarbonyl-ethyl)-pyrrolidine-1-carboxylic acid 2-chloro-benzyl ester

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) H₂, HCl; 2.) NaHCO₃ / 1.) PtO₂ / 1.) EtOH; 2.) H₂O

2: Lawesson's reagent / toluene / Heating

3: 1.) allyl bromide, Et₃N; 2.) Na(CN)BH₃, AcOH / 1.) CH₂Cl₂; 2.) MeOH

4: Et₃N / CH₂Cl₂

5: Et₃N / CH₂Cl₂

6: TFA / CH₂Cl₂

With Lawessons reagent; hydrogenchloride; hydrogen; sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid; triethylamine; allyl bromide; trifluoroacetic acid; platinum(IV) oxide; In dichloromethane; toluene;

DOI:10.1016/S0040-4039(98)01104-6

Reference yield:

tert-butyl (2S,4S)-1-(tert-butoxycarbonyl)-4-(cyanomethyl)pyroglutamate (153080-73-0) → (R)-3-((S)-2-Amino-2-tert-butoxycarbonyl-ethyl)-pyrrolidine-1-carboxylic acid 2-chloro-benzyl ester

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) H₂, HCl; 2.) NaHCO₃ / 1.) PtO₂ / 1.) EtOH; 2.) H₂O

2: Lawesson's reagent / toluene / Heating

3: 1.) allyl bromide, Et₃N; 2.) Na(CN)BH₃, AcOH / 1.) CH₂Cl₂; 2.) MeOH

4: Et₃N / CH₂Cl₂

5: TFA / CH₂Cl₂

With Lawessons reagent; hydrogenchloride; hydrogen; sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid; triethylamine; allyl bromide; trifluoroacetic acid; platinum(IV) oxide; In dichloromethane; toluene;

DOI:10.1016/S0040-4039(98)01104-6

upstream raw materials:

iodoacetonitrile

tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate

Downstream raw materials:

(R)-3-((S)-2-tert-Butoxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-pyrrolidine-1-carboxylic acid 2-chloro-benzyl ester

(R)-3-[(S)-2-tert-Butoxycarbonyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-pyrrolidine-1-carboxylic acid 2-chloro-benzyl ester