Trifluoroacetic acid → 2-(4-Chlorophenyl)-3-(4-{[(3-ethoxy-3-oxopropyl)amino]carbonyl}phenyl)hexanoic acid

HRID 2190891Notes

Reaction equation

HRID 2190891 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:16]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([NH:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:27])=[CH:22][CH:21]=2)[CH2:17][CH2:18][CH3:19])[C:9]([O:11]C(C)(C)C)=[O:10])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:16]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([NH:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:27])=[CH:22][CH:21]=2)[CH2:17][CH2:18][CH3:19])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58553819tert-Butyl 2-(4-chlorophenyl)-3-(4-{[(3-ethoxy-3-oxopropyl)amino]carbonyl}phenyl)hexanoate

Product 1

HCID 585538202-(4-Chlorophenyl)-3-(4-{[(3-ethoxy-3-oxopropyl)amino]carbonyl}phenyl)hexanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the slower-eluting diastereomer of tert-butyl 2-(4-chlorophenyl)-3-(4-{[(3-ethoxy-3-oxopropyl)amino]carbonyl}phenyl)hexanoate (1.9 g, 3.8 mmol) in DCM (20 mL) at 0° C. was added TFA (20 mL) over 1 min. After being stirred for 30 minutes, the solution was concentrated to afford the title compound. After being dried on high vacuum overnight, the material was used directly for the next step. LC1 2.09 min. (M+H)+ 446.

Workup

  1. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-1eaed69b41374710990a5e0d8ab55626
Source dataset
uspto-grants-2012_12
Patent number
US08324384B2

Reaction notes

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