Water → HCID 18473232, compound

HRID 2227388Notes

Reaction equation

HRID 2227388 reaction equation
C(O)(C(F)(F)F)=O.[Si]([O:15][CH2:16][CH2:17][CH2:18][C:19]([NH:35][S:36]([C:38]([CH3:41])([CH3:40])[CH3:39])=[O:37])([C:26]1[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[C:28]([F:34])[CH:27]=1)[C:20]1[N:24]([CH3:25])[CH:23]=[N:22][CH:21]=1)(C(C)(C)C)(C)C.O.C([O-])(O)=O.[Na+]>CC#N>[C:32]([C:29]1[CH:30]=[CH:31][C:26]([C:19]([NH:35][S:36]([C:38]([CH3:40])([CH3:39])[CH3:41])=[O:37])([C:20]2[N:24]([CH3:25])[CH:23]=[N:22][CH:21]=2)[CH2:18][CH2:17][CH2:16][OH:15])=[CH:27][C:28]=1[F:34])#[N:33]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 70136419HCID 70136419, compound

Product 1

HCID 18473232HCID 18473232, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

TFA (1 mL) was added to a solution of N-[4-{[tert-butyl(dimethyl)silyl]oxy}-1-(4-cyano-3-fluorophenyl)-1-(1-methyl-1H-imidazol-5-yl)butyl]-2-methylpropane-2-sulfinamide (0.111 g, 0.219 mmol) in CH3CN ( ): H2O (20 mL) with stirring at ambient temperature. After 0.5 h aqueous saturated NaHCO3 solution was added, the CH3CN was removed in vacuo, and the residue was chromatographed on a Chiralcel AD column eluting with 90/10, hexane/EtOH to give the two diastereomers of the title compound. MS(M+1) 393.

Workup

  1. customthe CH3CN was removed in vacuo
  2. customthe residue was chromatographed on a Chiralcel AD column
  3. washeluting with 90/10, hexane/EtOH

Sources & evidence

ORD record
ord-bfb7606d59814f0b92845952eb5f6135
Source dataset
uspto-grants-2002_07
Patent number
US06413964B1

Reaction notes

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