Methanol → HCID 86660737, compound

HRID 932205Notes

Reaction equation

HRID 932205 reaction equation
I([O-])(=O)(=O)=O.[Na+].[Cl:7][C:8]1[CH:9]=[C:10]([C@@H:14]2[C@@H:19]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[N:18]([C@@H:27]([CH:36]3[CH2:38][CH2:37]3)[CH2:28][NH:29][S:30]([CH:33]3[CH2:35][CH2:34]3)(=[O:32])=[O:31])[C:17](=[O:39])[C@:16]([CH2:42][CH:43]([OH:46])CO)([CH2:40][CH3:41])[CH2:15]2)[CH:11]=[CH:12][CH:13]=1.CO>O.C1COCC1.[Na+].[Cl-]>[Cl:7][C:8]1[CH:9]=[C:10]([C@@H:14]2[C@@H:19]([C:20]3[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=3)[N:18]([C@@H:27]([CH:36]3[CH2:38][CH2:37]3)[CH2:28][NH:29][S:30]([CH:33]3[CH2:34][CH2:35]3)(=[O:32])=[O:31])[C:17](=[O:39])[C@@:16]([CH2:40][CH3:41])([CH2:42][CH:43]=[O:46])[CH2:15]2)[CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 23667635Sodium periodateHCID 67999001HCID 67999001, compound

Product 1

HCID 86660737HCID 86660737, compoundYield 116.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5234Sodium ChlorideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium periodate (89 mg, 0.418 mmol) was added to a clear solution of N-((2S)-2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-(2,3-dihydroxypropyl)-3-ethyl-2-oxopiperidin-1-yl)-2-cyclopropylethyl)cyclopropanesulfonamide (Example 254, Step B, 85 mg, 0.14 mmol) in water (0.5 mL) and THF (1 mL). After several minutes, a solid formed. Methanol (1 ml) was added and the resulting emulsion was stirred for 30 min. The reaction was diluted with sat. aq. NaCl solution and extracted twice with ethyl acetate. The combined organic layers were washed with sat. aq. NaCl solution, dried over sodium sulfate and concentrated under the reduced pressure to provide the title compound (94 mg) which was used without purification in the next step. Mass Spectrum (ESI) m/z=577.0 (M+1)

Workup

  1. waitAfter several minutes
  2. customa solid formed
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic layers were washed with sat. aq. NaCl solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under the reduced pressure

Sources & evidence

ORD record
ord-74132c556d7245e9afd5250ceaebc394
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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