Trifluoroacetic acid → 3-(1-(2-(Benzyloxy)-2-oxoethyl)cyclopentanecarboxamido)-4-(biphenyl-4-yl)butanoic acid

HRID 333305Notes

Reaction equation

HRID 333305 reaction equation
[CH2:1]([O:8][C:9](=[O:41])[CH2:10][C:11]1([C:16]([NH:18][CH:19]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:31][CH:30]=2)[CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:41])[CH2:10][C:11]1([C:16]([NH:18][CH:19]([CH2:28][C:29]2[CH:30]=[CH:31][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:33][CH:34]=2)[CH2:20][C:21]([OH:23])=[O:22])=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67208776HCID 67208776, compound

Product 1

HCID 672087883-(1-(2-(Benzyloxy)-2-oxoethyl)cyclopentanecarboxamido)-4-(biphenyl-4-yl)butanoic acidYield 114.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxamido)-4-(biphenyl-4-yl)butanoate (38 mg, 0.068 mmol) in DCM (0.7 ml), TFA (0.263 ml, 3.42 mmol) was added. After stirred for 1 hour, the reaction mixture was concentrated to give 3-(1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxamido)-4-(biphenyl-4-yl)butanoic acid (39 mg); Retention time=1.73 minutes (condition B); MS (m+1)=500.4;

Workup

  1. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-0e0e206d0091475c964a225df19fdb0b
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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