Hydrochloric Acid → HCID 68556364, compound

HRID 1868148Notes

Reaction equation

HRID 1868148 reaction equation
C[O:2][C:3](=[O:33])[CH:4]([CH3:32])[CH2:5][C:6]1[S:7][C:8]([S:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=3[C:27]([F:30])([F:29])[F:28])[CH2:16][C@H:15]2[CH3:31])(=[O:13])=[O:12])=[CH:9][CH:10]=1.[Li+].[OH-].O.Cl>C1COCC1>[F:26][C:23]1[CH:24]=[CH:25][C:20]([N:17]2[CH2:18][CH2:19][N:14]([S:11]([C:8]3[S:7][C:6]([CH2:5][CH:4]([CH3:32])[C:3]([OH:33])=[O:2])=[CH:10][CH:9]=3)(=[O:12])=[O:13])[C@H:15]([CH3:31])[CH2:16]2)=[C:21]([C:27]([F:30])([F:28])[F:29])[CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 68547938HCID 68547938, compound

Product 1

HCID 68556364HCID 68556364, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[5-({(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl}sulfonyl)-2-thienyl]-2-methylpropanoic acid methyl ester (115 mg, 0.2 mmol) in THF (3 mL) was added LiOH (excess) and water (3 mL). The reaction mixture was stirred at rt overnight and acidified with 1N aq. HCl, then extracted with EtOAc. The organic layer was dried over Na2SO4. The crude product was purified on SiO2 column eluted with hexanes/EtOAc to give the titled compounds as a light yellow solid (94 mg, 95%). HRMS: calcd for C20H22F4N2O4S2+H+, 495.10299. found (ESI-FTMS, [M+H]1+), 495.10293.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customThe crude product was purified on SiO2 column
  4. washeluted with hexanes/EtOAc

Sources & evidence

ORD record
ord-91989bbe9aea4edd904042ba65b7f29d
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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