HCID 86590297, compound → HCID 69075736, compound

HRID 228136Notes

Reaction equation

HRID 228136 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([C:18]([N:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[N:32]([CH2:37][CH:38]3[CH2:40][CH2:39]3)[S:33]([CH3:36])(=[O:35])=[O:34])[CH2:22][CH2:21]2)=[O:19])[CH2:10][C:11]([O:13]C(C)(C)C)=[O:12])=[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]([C:18]([N:20]2[CH2:21][CH2:22][N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[N:32]([CH2:37][CH:38]3[CH2:40][CH2:39]3)[S:33]([CH3:36])(=[O:35])=[O:34])[CH2:24][CH2:25]2)=[O:19])[CH2:10][C:11]([OH:13])=[O:12])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86590297HCID 86590297, compound

Product 1

HCID 69075736HCID 69075736, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl (3S)-3-[(4-chlorophenyl)-methyl]-4-(4-{2-[(cyclopropylmethyl)-(methylsulfonyl)-amino]phenyl}piperazinyl)-4-oxobutanoate (Step 5) (0.16 g, 0.27 mmol) in 10 mL of 50% TFA in CH2Cl2 mixture was stirred at RT for 2 h. The volatile solvent was removed in vacuo. The residue was dissolved in CH2Cl2 and concentrated in vacuo. (3S)-3-[(4-Chlorophenyl)-methyl]-4-(4-{2-[(cyclopropylmethyl)-(methylsulfonyl)-amino]phenyl}piperazinyl)-4-oxobutanoic acid was obtained as a light yellow solid (0.14 g) MS (ESI, pos. ion) m/z: 534.4 (M+1). Calc'd for C26H32ClN3O5S: 533.18. Anal. Calc'd for C26H32ClN3O5S.1.5H2O: C, 55.66; H, 6.29; N, 7.49; Cl, 6.32. Found: C, 55.51; H, 5.85; N, 7.35; Cl, 6.12.

Workup

  1. customThe volatile solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d8d7de9b804845469b9be11fa48fc626
Source dataset
uspto-grants-2009_07
Patent number
US07560460B2

Reaction notes

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