3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl ester
• CAS No.: 777857-22-4
• Molecular Formula: C₂₅H₂₈N₂O₆
• Molecular Weight: 452.507

Synonyms:3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl ester

Chemical Property of 3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of 3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl ester

There total 4 articles about 3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl 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: 90.0%

di-tert-butyl dicarbonate (24424-99-5) + Nα-phenylmethoxycarbonyl-D-tryptophan methyl ester (130812-44-1) → 3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl ester (777857-22-4)

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane;

DOI:10.1039/b410180d

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → 3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl ester (777857-22-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / aq. NaOH

2: 90 percent / SO₂Cl

3: 90 percent / NaOH; Bu₄NHSO₄ / CH₂Cl₂

With sodium hydroxide; sulfuryl dichloride; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane;

DOI:10.1039/b410180d

Reference yield:

D-tryptophan (153-94-6,27732-43-0,80206-30-0,27813-82-7) → 3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl ester (777857-22-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / aq. NaOH

2: 90 percent / SO₂Cl

3: 90 percent / NaOH; Bu₄NHSO₄ / CH₂Cl₂

With sodium hydroxide; sulfuryl dichloride; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane;

DOI:10.1039/b410180d

upstream raw materials:

di-tert-butyl dicarbonate

N_α-phenylmethoxycarbonyl-D-tryptophan methyl ester

benzyl chloroformate

D-tryptophan

Downstream raw materials:

(2R,3aS,8aS)-3a-phenylselenyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 1-benzyl ester 8-tert-butyl ester 2-methyl ester

3a-hydroxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

3a-hydroxy-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 1-benzyl ester 8-tert-butyl ester 2-methyl ester

3a-phenylselanyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 1-benzyl ester 8-tert-butyl ester 2-methyl ester

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