Trifluoroacetic acid → n-[(1r)-1-[(4-Chlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}-piperidyl)-2-oxoethyl]((3s, 1r) 3-aminocyclopentyl)carboxamide

HRID 489652Notes

Reaction equation

HRID 489652 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:29][C:30]([C@@H:32]2[CH2:36][CH2:35][C@H:34]([NH:37]C(OC(C)(C)C)=O)[CH2:33]2)=[O:31])[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C@@H:9]([NH:29][C:30]([C@@H:32]2[CH2:36][CH2:35][C@H:34]([NH2:37])[CH2:33]2)=[O:31])[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:14][CH2:13]2)=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69151551HCID 69151551, compound

Product 1

HCID 10119929n-[(1r)-1-[(4-Chlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}-piperidyl)-2-oxoethyl]((3s, 1r) 3-aminocyclopentyl)carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 50 mL round-bottomed flask was added N-[(1R)-1-[(4-chlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)-amino]phenyl}-piperidyl)-2-oxoethyl]{(3S, 1R)-3-[(tert-butoxy)carbonylamino]-cyclopentyl)-carboxamide (Step a) (323 mg, 0.5 mmol) followed by a 50% soln of TFA in CH2Cl2 (20 mL). After stirring for 2 h, the solvent was removed in vacuo. Purification by preparative HPLC [Phenomenex; 5 μm 250×21.2 mm, 5% to 95% CH3CN (0.1% TFA) in H2O (0.1% TFA) over 30 min, then 100% CH3CN (0.1% TFA) for 2 min]provided the title compound (TFA salt) as a white foam (145 mg). MS (ESI, pos. ion) m/z: 547 (M+1); (ESI, neg. ion) 545 (M−1). Calc'd for C27H35ClN4O4S: 546.21. Anal. Calcd for C27H35ClN4O4S.1.2C2HF3O2: C, 51.63; H, 5.49; N, 8.19. Found: C, 51.69; H, 5.49; N, 8.14.

Workup

  1. customthe solvent was removed in vacuo
  2. customPurification by preparative HPLC [Phenomenex
  3. wait5 μm 250×21.2 mm, 5% to 95% CH3CN (0.1% TFA) in H2O (0.1% TFA) over 30 min

Sources & evidence

ORD record
ord-9508da57bb84403c8837817f501f2705
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

Loading…