Trifluoroacetic acid → HCID 53890485, compound

HRID 2297317Notes

Reaction equation

HRID 2297317 reaction equation
C([O:5][C:6](=[O:49])[CH2:7][C@H:8]([NH:31][C:32]([O:34][CH2:35][CH:36]1[C:48]2[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=2[C:42]2[C:37]1=[CH:38][CH:39]=[CH:40][CH:41]=2)=[O:33])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:47]1[C:48]2[CH:36]([CH2:35][O:34][C:32]([NH:31][C@H:8]([CH2:9][CH2:10][C:11]3[CH:12]=[CH:13][C:14]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:19][CH:18]=4)=[CH:15][CH:16]=3)[CH2:7][C:6]([OH:49])=[O:5])=[O:33])[C:37]3[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:43]=2[CH:44]=[CH:45][CH:46]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54022445HCID 54022445, compound

Product 1

HCID 53890485HCID 53890485, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (R)-3-(9-fluorenylmethoxycarbonyl-amino)-5-(4′-heptyloxybiphenyl-4-yl)pentanoic acid tert-butyl ester (crude, 3.34 g) in CH2Cl2 (20 ml) was added TFA (20 ml) dropwise. After being stirred for 1 h at room temperature, the mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel (MeOH/CH2Cl2, 1:20) to give (R)-3-(9-fluorenylmethoxycarbonylamino)-5-(4′-heptyloxybiphenyl-4-yl)pentanoic acid (2.07 g, 77% in 3 steps) as a white amorphous powder.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was purified by column chromatography on silica gel (MeOH/CH2Cl2, 1:20)

Sources & evidence

ORD record
ord-c41af00b52be4e7fb81a7cdf02920bea
Source dataset
uspto-grants-2002_12
Patent number
US06489440B1

Reaction notes

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