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

HRID 489654Notes

Reaction equation

HRID 489654 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 23587435n-[(1r)-1-[(4-Chlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)-amino]phenyl}-piperidyl)-2-oxoethyl]{(1s,3r)-3-[(tert-butoxy)carbonylamino]-cyclopentyl}-carboxamide

Product 1

HCID 10119930n-[(1r)-1-[(4-Chlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}-piperidyl)-2-oxoethyl]((1s,3r)-3-aminocyclopentyl)carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure described in Example 3 Step (b) from N-[(1R)-1-[(4-chlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)-amino]phenyl}-piperidyl)-2-oxoethyl]{(1S,3R)-3-[(tert-butoxy)carbonylamino]-cyclopentyl}-carboxamide (Step a) (323 mg, 0.5 mmol) and a 50% soln of TFA in CH2Cl2 (20 mL). 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 (113 mg). MS (ESI, pos. ion) m/z: 547 (M+1); (ESI, neg. ion) m/z: 545 (M-1). Calc'd for C27H35ClN4O4S: 546.21.

Workup

  1. customThe title compound was prepared
  2. customPurification by preparative HPLC [Phenomenex

Sources & evidence

ORD record
ord-57660289e4ee492f8ae9f0c0599a3b1a
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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