Acetic Acid → HCID 58966622, compound

HRID 14230Notes

Reaction equation

HRID 14230 reaction equation
[CH2:1]([S:4][C:5]1[CH:6]=[C:7]([CH:36]=[CH:37][CH:38]=1)[C:8]([NH:10][C@@H:11]([CH2:27][C:28]1[CH:33]=[C:32]([F:34])[CH:31]=[C:30]([F:35])[CH:29]=1)[C@H:12]([OH:26])[CH2:13][NH:14][C:15]1([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH3:25])[CH:19]=2)[CH2:17][CH2:16]1)=[O:9])[CH:2]=[CH2:3].CC(O)=[O:41].C1C=C(Cl)C=C(C(OO)=O)C=1>C(Cl)Cl.CCOCC>[CH2:1]([S:4]([C:5]1[CH:6]=[C:7]([CH:36]=[CH:37][CH:38]=1)[C:8]([NH:10][C@@H:11]([CH2:27][C:28]1[CH:29]=[C:30]([F:35])[CH:31]=[C:32]([F:34])[CH:33]=1)[C@H:12]([OH:26])[CH2:13][NH:14][C:15]1([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH3:25])[CH:19]=2)[CH2:17][CH2:16]1)=[O:9])=[O:41])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 70297m-Chloroperbenzoic acid2×HCID 58802454HCID 58802454, compound

Product 1

HCID 58966622HCID 58966622, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

3-(allylthio)-N-((1S,2R)-1-(3,5-difluorobenzyl)-3-{[1-(3-ethylphenyl)cyclopropyl]amino}-2-hydroxypropyl)benzamide (325 mg, 0.606 mmol) was dissolved in CH2Cl2 (10 mL) and AcOH (1 mL) and treated with mCPBA (104 mg, 0.606 mmol). The reaction mixture was stirred for 2.5 h, at which time more mCPBA (20 mg, 0.11 mmol) was added and stirring continued for 30 min. more. The organic layer was diluted with Et2O and washed with 15% sodium thiosulfite solution. The organic was washed with brine, then dried (MgSO4) and concentrated to give an oil, which was chromatographed with 25% to 50% EtOAc in hexanes to give the title compound. (LRMS (M+H) m/z 553.8)

Workup

  1. additionwas added
  2. washwashed with 15% sodium thiosulfite solution
  3. washThe organic was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give an oil, which
  7. customwas chromatographed with 25% to 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-efb9c98ad02a43808b9af6d69e065537
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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