Methanol → HCID 86660737, compound

HRID 1048519Notes

Reaction equation

HRID 1048519 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-a06ece1220b043198c921d687eda1286
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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