HCID 53729896, compound → HCID 53732363, compound

HRID 2296674Notes

Reaction equation

HRID 2296674 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][S:7]([N:10]1[CH2:15][CH2:14][N:13]([S:16]([C:19]2[S:20][C:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[CH:22][CH:23]=2)(=[O:18])=[O:17])[C@@H:12]([C:31]([NH:33][O:34]C(C)(C)C)=[O:32])[CH2:11]1)(=[O:9])=[O:8])(=[O:3])[CH3:2]>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.O>[C:1]([NH:4][CH2:5][CH2:6][S:7]([N:10]1[CH2:15][CH2:14][N:13]([S:16]([C:19]2[S:20][C:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[CH:22][CH:23]=2)(=[O:17])=[O:18])[C@@H:12]([C:31]([NH:33][OH:34])=[O:32])[CH2:11]1)(=[O:9])=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 1

HCID 53729896HCID 53729896, compound

Product 1

HCID 53732363HCID 53732363, compoundYield 74.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

A mixture of (2R)-4-[2-(acetylamino)ethanesulfonyl]-N-tert-butoxy-1-[5-(4-fluorophenyl)thiophene-2-sulfonyl]-2-piperazinecarboxamide (130 mg) in anisole (1 ml), trifluoroacetic acid (1 ml) and H2O (0.02 ml) was stirred at ambient temperature overnight, and then at 50 ° C. for 5 hours. The mixture was concentrated in vacuo, and the residue was purified by SiO2 column chromatography, eluted with MeOH in CHCl3=2% then 5%. The fractions containing the desired product were combined and concentrated in vacuo. The residue was triturated with diisopropyl ether to give 88 mg of (2R)-4-[2-(acetylamino)ethanesulfonyl]-1-(5-(4-fluorophenyl)thiophene-2-sulfonyl]-N-hydroxy-2-piperazinecarboxamide.

Workup

  1. waitat 50 ° C. for 5 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified by SiO2 column chromatography
  4. washeluted with MeOH in CHCl3=2%
  5. additionThe fractions containing the desired product
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-324700230d154aa8a0772f316cd94d81
Source dataset
uspto-grants-2002_12
Patent number
US06489324B2

Reaction notes

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