Hydrogen Peroxide → HCID 117389010, compound
Reaction equation
C([C@@H]1COC(=O)N1[C:14](=[O:41])[C@@H:15]([C:29]1[CH:34]=[CH:33][C:32]([S:35]([CH:38]2[CH2:40][CH2:39]2)(=[O:37])=[O:36])=[CH:31][CH:30]=1)[CH2:16][C@H]1CCN(C(OC(C)(C)C)=O)C1)C1C=CC=CC=1.[OH-].[Li+].OO.S([O-])([O-])=[O:47].[Na+].[Na+]>O1CCCC1.O>[CH:38]1([S:35]([C:32]2[CH:31]=[CH:30][C:29]([CH:15]([CH3:16])[C:14]([OH:41])=[O:47])=[CH:34][CH:33]=2)(=[O:36])=[O:37])[CH2:39][CH2:40]1Participants
Procedure
(S)-tert-Butyl 3-((R)-3-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-(4-(cyclopropylsulfonyl)phenyl)-3-oxopropyl)pyrrolidine-1-carboxylate (1.38 g, 2.36 mmol) was dissolved in a mixed solvent of tetrahydrofuran and water (3: 1, 12.8 mL), and an aqueous solution (1.9 mL) consisting of lithium hydroxide (113 mg, 4.72 mmol) and a hydrogen peroxide solution (30%, 1.10 mL) was added to the above obtained solution under ice-cold condition. The obtained mixture was stirred for 1 hour. Thereafter, an aqueous solution of sodium sulfite was added to the reaction solution, and the mixed solution was then washed with diethyl ether. The reaction solution was neutralized with a 0.5 M aqueous solution of hydrochloric acid, and was then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and was then concentrated in vacuo, so as to obtain (R)-3-((S)-1-tert-butoxycarbonyl)pyrrolidin-3-yl)-2-(4-(cyclopropylsulfonyl)phenyl)propanoic acid (910 mg, 85%) in the form of a white solid.
Workup
- washthe mixed solution was then washed with diethyl ether
- extractionwas then extracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationwas then concentrated in vacuo
Sources & evidence
- ORD record
- ord-391a809b32a843ef981b3b619b3799b1
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242978B2
Reaction notes
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