tert-Butanol → HCID 67999001, compound

HRID 932204Notes

Reaction equation

HRID 932204 reaction equation
[CH2:1]([C@@:4]1(CC)[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH:33]2[CH2:35][CH2:34]2)[CH2:25][NH:26][S:27]([CH:30]2[CH2:32][CH2:31]2)(=[O:29])=[O:28])[C:5]1=[O:36])[CH:2]=C.C[N+]1([O-])CC[O:43]CC1.[C:47]([OH:51])(C)([CH3:49])[CH3:48]>C1COCC1.O.C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[Cl:16][C:12]1[CH:11]=[C:10]([C@@H:8]2[C@@H:7]([C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)[N:6]([C@@H:24]([CH:33]3[CH2:35][CH2:34]3)[CH2:25][NH:26][S:27]([CH:30]3[CH2:32][CH2:31]3)(=[O:29])=[O:28])[C:5](=[O:36])[C@:4]([CH2:48][CH:47]([OH:51])[CH2:49][OH:43])([CH2:1][CH3:2])[CH2:9]2)[CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 3

HCID 6386tert-Butanol2×HCID 82029Methyl morpholine oxideHCID 68000393HCID 68000393, compound

Product 1

HCID 67999001HCID 67999001, compound

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-((S)-2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-ethyl-2-oxopiperidin-1-yl)-2-cyclopropylethyl)cyclopropanesulfonamide (Example 254, Step A, 80 mg, 0.139 mmol) in THF (375 μL), water (250 μL) and t-butanol (208 μL) was treated with 4-methylmorpholine N-oxide (57.0 mg, 0.486 mmol) followed by 2.5% osmium tetroxide in t-butanol (45.6 μL, 3.47 μmol). After stirring at ambient temperature for 16 h, the mixture was diluted with ethyl acetate and washed with water and sat. aq. NaCl solution. The organic layer was dried over sodium sulfate and concentrated to provide the title compound as a mixture of diastereomers (85 mg) which was used directly in the next step. Mass Spectrum (ESI) m/z=609.1 (M+1)

Workup

  1. washwashed with water and sat. aq. NaCl solution
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ae571942543d44af8927f76aee702da1
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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