(S)-2-tert-Butoxycarbonylamino-pentanedioic acid 1-[(benzhydryl-carbamoyl)-methyl] ester

Base Information

• Chemical Name: (S)-2-tert-Butoxycarbonylamino-pentanedioic acid 1-[(benzhydryl-carbamoyl)-methyl] ester
• CAS No.: 200399-54-8
• Molecular Formula: C₂₅H₃₀N₂O₇
• Molecular Weight: 470.522
• Mol file: 200399-54-8.mol

Synonyms:(S)-2-tert-Butoxycarbonylamino-pentanedioic acid 1-[(benzhydryl-carbamoyl)-methyl] ester

Chemical Property of (S)-2-tert-Butoxycarbonylamino-pentanedioic acid 1-[(benzhydryl-carbamoyl)-methyl] ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-tert-Butoxycarbonylamino-pentanedioic acid 1-[(benzhydryl-carbamoyl)-methyl] ester

There total 1 articles about (S)-2-tert-Butoxycarbonylamino-pentanedioic acid 1-[(benzhydryl-carbamoyl)-methyl] 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: 73.0%

Boc-Glu (2419-94-5) + N-benzhydryl-2-bromoacetamide (119706-03-5) → (S)-2-tert-Butoxycarbonylamino-pentanedioic acid 1-[(benzhydryl-carbamoyl)-methyl] ester (200399-54-8)

Guidance literature:

With 15-crown-5; sodium methylate; In ethyl acetate; at 50 ℃; for 3h;

DOI:10.1016/S0968-0896(97)00141-7

Reference yield:

(S)-2-tert-Butoxycarbonylamino-pentanedioic acid 1-[(benzhydryl-carbamoyl)-methyl] ester (200399-54-8) → (7S,9aS)-4,9-Dioxo-decahydro-3a,8-diaza-cyclopentacyclooctene-7-carboxylic acid (benzhydryl-carbamoyl)-methyl ester (200399-56-0)

Guidance literature:

Multi-step reaction with 5 steps

1: DCC / tetrahydrofuran / Ambient temperature

2: 73.3 percent / MeONa, 15-crown-5 / dimethylformamide / Ambient temperature

3: DCC / tetrahydrofuran / 3 h / Ambient temperature

4: 4 N HCl / dioxane / 0.5 h

5: Et₃N / acetonitrile / 3 h / Ambient temperature

With hydrogenchloride; 15-crown-5; sodium methylate; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0968-0896(97)00141-7

Reference yield:

(S)-2-tert-Butoxycarbonylamino-pentanedioic acid 1-[(benzhydryl-carbamoyl)-methyl] ester (200399-54-8) → (S)-1-{(S)-4-[(Benzhydryl-carbamoyl)-methoxycarbonyl]-4-tert-butoxycarbonylamino-butyryl}-pyrrolidine-2-carboxylic acid (200399-55-9)

Guidance literature:

Multi-step reaction with 2 steps

1: DCC / tetrahydrofuran / Ambient temperature

2: 73.3 percent / MeONa, 15-crown-5 / dimethylformamide / Ambient temperature

With 15-crown-5; sodium methylate; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(97)00141-7

upstream raw materials:

Boc-Glu

N-benzhydryl-2-bromoacetamide

Downstream raw materials:

(7S,9aS)-4,9-Dioxo-decahydro-3a,8-diaza-cyclopentacyclooctene-7-carboxylic acid (benzhydryl-carbamoyl)-methyl ester

(S)-1-{(S)-4-[(Benzhydryl-carbamoyl)-methoxycarbonyl]-4-tert-butoxycarbonylamino-butyryl}-pyrrolidine-2-carboxylic acid