Trifluoroacetic acid → CbzNH-PEG6-CH2COOH

HRID 1726836Notes

Reaction equation

HRID 1726836 reaction equation
C(O)(C(F)(F)F)=[O:2].C([O:12][C:13](=[O:44])[CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][NH:33][C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35])(C)(C)C>C(Cl)Cl>[NH4+:33].[OH-:2].[CH2:37]([O:36][C:34]([NH:33][CH2:32][CH2:31][O:30][CH2:29][CH2:28][O:27][CH2:26][CH2:25][O:24][CH2:23][CH2:22][O:21][CH2:20][CH2:19][O:18][CH2:17][CH2:16][O:15][CH2:14][C:13]([OH:44])=[O:12])=[O:35])[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69074603{2-[2-(2-{2-[2-(2-Benzyloxycarbonylamino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-acetic acid tert-butyl ester

Product 2

HCID 14923Ammonium HydroxideYield 30%HCID 69076282CbzNH-PEG6-CH2COOHYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (4 mL) was added to a solution of compound 6 (0.93 g, 1.7 mmol) in CH2Cl2 (20 mL) and the resulting solution was stirred overnight at ambient temperature. The resulting solution was concentrated in vacuo and the residue was loaded onto a silica gel gravity column (50 g) and eluted with CH2Cl2:MeOH:NH4OH (30% aqueous) 90:10:1 (v/v) to afford compound 7 as a thick colorless oil (0.83 g, 99%).

Workup

  1. concentrationThe resulting solution was concentrated in vacuo
  2. washeluted with CH2Cl2

Sources & evidence

ORD record
ord-8a4fd569148544a9aeddfea59e5c53ac
Source dataset
uspto-grants-2009_02
Patent number
US07494714B2

Reaction notes

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