Methyl morpholine oxide → HCID 21084077, compound

HRID 347920Notes

Reaction equation

HRID 347920 reaction equation
[CH2:1]([NH:4][C:5]([C:7]1[S:22][C:10]2[N:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12](=[O:15])[CH:13]=[CH:14][C:9]=2[C:8]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:6])[CH:2]=C.C[N+]1([O-])CC[O:33]CC1.[C:37]([O-:40])(O)=O.[Na+]>O=[Os](=O)(=O)=O.CC(C)=O.O>[OH:33][CH:2]([CH2:37][OH:40])[CH2:1][NH:4][C:5]([C:7]1[S:22][C:10]2[N:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12](=[O:15])[CH:13]=[CH:14][C:9]=2[C:8]=1[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:6]

Participants

6

Reactant 3

HCID 82029Methyl morpholine oxideHCID 516892Sodium BicarbonateHCID 21084086HCID 21084086, compound

Product 1

HCID 21084077HCID 21084077, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a stirred solution of the compound of Example 95 (50 mg) in 8:1 acetone-water (10 mL) was added 4-methylmorpholine N-oxide (100 mg) followed by a catalytic amount of OsO4. The reaction mixture was stirred for 16 h and then poured into saturated NaHCO3 solution (20 mL). The product was extracted with DCM (2×20 mL) and the combined organic fractions dried over MgSO4, filtered and solvent removed in vacuo. The crude product was purified by column chromatography (silica, 10% EtOH in DCM) to give the title compound as a solid (32 mg). δH (CDCl3) 7.8–7.1 (11H, m), 6.44 (1H, d, J 10 Hz), 5.62 (1H, bs), 3.7–3.1 (5H, m). LCMS (ES+) 421 (M+H)+.

Workup

  1. extractionThe product was extracted with DCM (2×20 mL)
  2. dry with materialthe combined organic fractions dried over MgSO4
  3. filtrationfiltered
  4. customsolvent removed in vacuo
  5. customThe crude product was purified by column chromatography (silica, 10% EtOH in DCM)

Sources & evidence

ORD record
ord-f34eed12ff5747868d470ca687eff6b6
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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