Trifluoroacetic acid → HCID 10208130, compound

HRID 489656Notes

Reaction equation

HRID 489656 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:29][C:30]([CH:32]2[CH2:35][N:34](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:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:29][C:30]([CH:32]2[CH2:35][NH:34][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

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69152150HCID 69152150, compound

Product 1

HCID 10208130HCID 10208130, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure described in Example 3 (Step b) from tert-butyl 3-(N-[(1R)-1-[(4-chlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)-amino]phenyl}-piperidyl)-2-oxoethyl]-carbamoyl)azetidinecarboxylate (Step a) (309 mg, 0.5 mmol) and 50% TFA in CH2Cl2 (20 mL). Purification by preparative reverse phase 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 (205 mg). MS (ESI, pos. ion) m/z: 519 (M+1); (ESI, neg. ion) m/z: 517 (M−1). Calc'd for C25H31ClN4O4S: 518.18. Anal. Calcd for C25H11ClN4O4S 1.4C2HF3O2: C, 49.20; H, 4.81; N, 8.26. Found: C, 49.31; H, 4.91; N, 8.25.

Workup

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

Sources & evidence

ORD record
ord-54b04215d3d5445693bd28b1dda4eac6
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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