Water → HCID 69752020, compound

HRID 1062394Notes

Reaction equation

HRID 1062394 reaction equation
[OH:1]OS([O-])=O.[K+].[Cl:7][C:8]1[CH:13]=[C:12]([S:14][CH2:15][CH:16]=[CH2:17])[CH:11]=[CH:10][C:9]=1[NH:18][C:19](=[O:27])[C@:20]([OH:26])([CH3:25])[C:21]([F:24])([F:23])[F:22].[OH2:28]>CO>[Cl:7][C:8]1[CH:13]=[C:12]([S:14]([CH2:15][CH:16]=[CH2:17])(=[O:1])=[O:28])[CH:11]=[CH:10][C:9]=1[NH:18][C:19](=[O:27])[C@:20]([OH:26])([CH3:25])[C:21]([F:24])([F:22])[F:23]

Participants

5

Reactant 3

HCID 962Water2×HCID 23707502Potassium hydroxy sulfiteHCID 53846499HCID 53846499, compound

Product 1

HCID 69752020HCID 69752020, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Oxone (1.44 g) in water (15 ml) was added to a solution of (R)-N-{2-chloro-4-(2-propenylsulphanyl)phenyl}-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 407) (0.389 g) in methanol (15 ml). The mixture was stirred for 1.5 hours. Water (50 ml) was added and the mixture extracted into ethyl acetate (100 ml) and dried. Volatile material was removed by evaporation and the residue purified on a silica gel Mega Bond Elut column eluting with 20-30% ethyl acetate/iso-hexane to give the title compound as a foam (0.180 g). NMR: 1.61 (s, 3H), 4.18 (d, 2H), 5.18-5.32 (m, 2H), 5.61-5.75 (m, 1H), 7.82-7.85 (m, 1H), 7.98 (s, 1H), 8.01 (s, 1H), 8.33 (d, 1H), 9.91 (s, 1H); MS (ESP−): 370.

Workup

  1. extractionthe mixture extracted into ethyl acetate (100 ml)
  2. customdried
  3. customVolatile material was removed by evaporation
  4. customthe residue purified on a silica gel Mega Bond Elut column
  5. washeluting with 20-30% ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-971b76357df84eb2b760289b6586bc54
Source dataset
uspto-grants-2005_11
Patent number
US06960688B2

Reaction notes

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