2,2,2-Trichloroethyl chloroformate → 4-[(Benzyl)-(2,2,2-trichloro-ethoxycarbonyl)-amino]-pyrrolidine-1,2-dicarboxylicacid 1-tert-butyl ester 2-methyl ester

HRID 490575Notes

Reaction equation

HRID 490575 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][N:6]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:4].[C:25](Cl)([O:27][CH2:28][C:29]([Cl:32])([Cl:31])[Cl:30])=[O:26]>C(Cl)Cl>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([N:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:25]([O:27][CH2:28][C:29]([Cl:32])([Cl:31])[Cl:30])=[O:26])[CH2:7][N:6]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:4]

Participants

4

Reactant 2

HCID 870632,2,2-Trichloroethyl chloroformateHCID 67549475HCID 67549475, compound

Product 1

HCID 675466644-[(Benzyl)-(2,2,2-trichloro-ethoxycarbonyl)-amino]-pyrrolidine-1,2-dicarboxylicacid 1-tert-butyl ester 2-methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of a corresponding 4-[(benzylamino)]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester in DCM, cooled to 0 degree is added TrocCl and TEA. The mixture is stirred overnight, washed with Na2CO3, brine, dried and concentrated in vacuo to give 4-[(benzyl)-(2,2,2-trichloro-ethoxycarbonyl)-amino]-pyrrolidine-1,2-dicarboxylicacid 1-tert-butyl ester 2-methyl ester (19).

Workup

  1. washwashed with Na2CO3, brine
  2. customdried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ab01a09b53145d8bc068bc1245185f8
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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