Hydrogen Peroxide → HCID 58485336, compound

HRID 1046250Notes

Reaction equation

HRID 1046250 reaction equation
OO.[OH:3][C:4]([CH3:39])([CH3:38])[CH2:5][C@@:6]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:11][C:10](=[O:12])[N:9]([C@H:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([CH3:31])([CH3:30])[C:28]#[N:29])=[N:25][CH:26]=3)=[CH:17][CH:16]=2)[CH3:14])[CH2:8][CH2:7]1.C([O-])([O-])=[O:41].[K+].[K+].[O-]S([O-])(=S)=O.[Na+].[Na+]>>[OH:3][C:4]([CH3:38])([CH3:39])[CH2:5][C@@:6]1([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[O:11][C:10](=[O:12])[N:9]([C@H:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([CH3:30])([CH3:31])[C:28]([NH2:29])=[O:41])=[N:25][CH:26]=3)=[CH:17][CH:16]=2)[CH3:14])[CH2:8][CH2:7]1

Participants

5

Reactant 4

HCID 784Hydrogen Peroxide2×HCID 11430Potassium Carbonate2×HCID 24477Sodium ThiosulfateHCID 58485358HCID 58485358, compound

Product 1

HCID 58485336HCID 58485336, compound

Procedure

Hydrogen peroxide (35% in water, 0.1 mL) was added to a mixture of 2-[5-(4-{(S)-1-[(S)-6-(2-hydroxy-2-methyl-propyl)-2-oxo-6-phenyl-[1,3]oxazinan-3-yl]-ethyl}-phenyl)-pyridin-2-yl]-2-methyl-propionitrile (0.21 g; for preparation see Example 194) and K2CO3 (0.03 g) in ddimethyl sulfoxide (2 mL) at room temperature. After stirring the mixture for 3 h at room temperature, another portion of hydrogen peroxide (35% in water, 0.1 mL) and K2CO3 (0.03 g) were added. The mixture was further stirred at room temperature for 1 h and at 40° C. overnight. After cooling to room temperature, little aqueous Na2S2O3 solution was added and then the mixture was concentrated. The residue was purified by HPLC on reversed phase (methanol/water/ammonia) to furnish the title compound. Yield: 0.03 g (14% of theory); Mass spectrum (ESI+): m/z=516 [M+H]+.

Workup

  1. stirringThe mixture was further stirred at room temperature for 1 h and at 40° C. overnight
  2. temperatureAfter cooling to room temperature
  3. concentrationthe mixture was concentrated
  4. customThe residue was purified by HPLC on reversed phase (methanol/water/ammonia)

Sources & evidence

ORD record
ord-d31aff7e29fb4c6a9fd80131dfd348da
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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