Sodium Methoxide → HCID 59458380, compound

HRID 1874238Notes

Reaction equation

HRID 1874238 reaction equation
C[O-].[Na+].[Si]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([NH:40][S@@:41]([C:43]([CH3:46])([CH3:45])[CH3:44])=[O:42])([C:26]2[CH:31]=[C:30]([O:32][C:33]([F:38])([F:37])[CH:34]([F:36])[F:35])[CH:29]=[C:28]([F:39])[CH:27]=2)[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:14][C:13]=1[F:47])(C(C)(C)C)(C)C>>[F:47][C:13]1[CH:14]=[C:15]([C:18]([NH:40][S@@:41]([C:43]([CH3:46])([CH3:45])[CH3:44])=[O:42])([C:26]2[CH:31]=[C:30]([O:32][C:33]([F:37])([F:38])[CH:34]([F:35])[F:36])[CH:29]=[C:28]([F:39])[CH:27]=2)[CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:16]=[CH:17][C:12]=1[OH:11]

Participants

3

Reactant 2

HCID 10942334Sodium MethoxideHCID 59458397HCID 59458397, compound

Product 1

HCID 59458380HCID 59458380, compoundYield 87%

Procedure

At room temperature a solution of NaOMe (5 mL, 0.5 M solution in MeOH) was added to the 4:1 diastereomeric mixture of (R)—N-(1-(4-(tert-butyldimethylsilyloxy)-3-fluorophenyl)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-phenylethyl)-2-methylpropane-2-sulfinamide (801 mg, 1.22 mmol). The reaction mixture was stirred for 15 minutes, MeOH was removed then the residue dissolved in EtOAc (50 mL) and transferred to a separation funnel HCl (20 mL, 1.0 N solution) was added and the EtOAc layer was separated. The aqueous layer was extracted with EtOAc (2×10 mL) and the combined organic layers were dried over Na2SO4, filtered and concentrated to yield (R)—N-(1-(3-fluoro-4-hydroxyphenyl)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-phenylethyl)-2-methylpropane-2-sulfinamide as a white foam (578 mg, 87% yield). LCMS: RT=1.987 min [M+H] 546.35 (Phenomenex Luna C18 column, 4.6×30 mm eluting with 10-90% MeOH/H2O over 2 minutes containing 0.1% TFA; 5 mL/min, monitoring at 220 nm).

Workup

  1. customMeOH was removed
  2. dissolutionthe residue dissolved in EtOAc (50 mL)
  3. customtransferred to a separation funnel
  4. additionHCl (20 mL, 1.0 N solution) was added
  5. customthe EtOAc layer was separated
  6. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  7. dry with materialthe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c42379f334c44dbe9e89509fb4a32780
Source dataset
uspto-grants-2012_11
Patent number
US08304403B2

Reaction notes

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