Trifluoroacetic acid → 3-(1-(Carboxymethyl)cyclopentanecarboxamido)-2-(3,4-dichlorobenzyl)propanoic acid

HRID 333295Notes

Reaction equation

HRID 333295 reaction equation
C([O:5][C:6](=[O:30])[CH:7]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=1)[CH2:8][NH:9][C:10]([C:12]1([CH2:17][C:18]([OH:20])=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:18]([CH2:17][C:12]1([C:10]([NH:9][CH2:8][CH:7]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=2)[C:6]([OH:30])=[O:5])=[O:11])[CH2:16][CH2:15][CH2:14][CH2:13]1)([OH:20])=[O:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 687477812-(1-(3-Tert-butoxy-2-(3,4-dichlorobenzyl)-3-oxopropylcarbamoyl)cyclopentyl)acetic acid

Product 1

HCID 687483013-(1-(Carboxymethyl)cyclopentanecarboxamido)-2-(3,4-dichlorobenzyl)propanoic acidYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(1-(3-tert-butoxy-2-(3,4-dichlorobenzyl)-3-oxopropylcarbamoyl)cyclopentyl)acetic acid (30.6 mg, 0.067 mmol) in DCM (0.7 ml), TFA (0.257 ml, 3.34 mmol) was added. The reaction mixture was allowed to stir for 2 hr and then concentrated under reduced pressure. The obtained residue was purified by RP-HPLC (SunFire, H2O (0.1% TFA) I CH3CN), and then lyophilized to give 3-(1-(carboxymethyl)cyclopentanecarboxamido)-2-(3,4-dichlorobenzyl)propanoic acid (10.5 mg); Retention time=0.67 minutes (condition B); MS (m+1)=402.0; 1H NMR (400 MHz, DMSO-d6, mixture of rotamers) δ ppm 1.47-1.58 (m, 6H) 1.97-2.04 (m, 2H) 2.54-2.63 (m, 2H) 2.68-2.84 (m, 3H) 3.13-3.28 (m, 2H) 7.17-7.19 (m, 1H) 7.43 (d, J=2.0 Hz, 1H) 7.52-7.54 (m, 1H) 7.61-7.63 (app t, 1H) 12.14 (br s, 2H); HRMS (ES+) m/z for C18H22Cl2NO5 [M+H]+ calcd 402.0875. found 402.0855.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe obtained residue was purified by RP-HPLC (SunFire, H2O (0.1% TFA) I CH3CN)

Sources & evidence

ORD record
ord-8b013eee0bdb4687817055bccfa46f38
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

Loading…