Hydrogen Peroxide → (S)-3-(tert-butoxycarbonyl(isopropyl)amino)-2-(5-chlorothiophen-2-yl)propanoic acid

HRID 2200314Notes

Reaction equation

[OH-:1].[Li+].OO.C([C@@H]1COC(=O)N1[C:18](=[O:38])[C@@H:19]([C:32]1[S:33][C:34]([Cl:37])=[CH:35][CH:36]=1)[CH2:20][N:21]([CH:29]([CH3:31])[CH3:30])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])C1C=CC=CC=1>O.C1COCC1>[C:24]([O:23][C:22]([N:21]([CH:29]([CH3:30])[CH3:31])[CH2:20][C@H:19]([C:32]1[S:33][C:34]([Cl:37])=[CH:35][CH:36]=1)[C:18]([OH:38])=[O:1])=[O:28])([CH3:25])([CH3:26])[CH3:27]

Participants

Conditions

Temperature: -5 °C

Procedure

A mixture solution of lithium hydroxide (374 mg, 15.6 mmol) in H2O (60 mL) and 30% hydrogen peroxide (1.60 mL, 15.6 mmol) was added dropwise to a solution of tert-butyl (S)-3-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-(5-chlorothiophen-2-yl)-3-oxopropyl(isopropyl)carbamate (7.54 g, 14.9 mmol) in THF (150 mL) at −5° C. The mixture was stirred at −5° C. After 10 minutes, the reaction was quenched with 10% Na2SO3 (16 mL) at −5° C. and stirred at room temperature for 30 minutes. The THF was removed in vacuo. The aqueous layer was acidified with 1M NaH2PO4 and extracted with DCM (3×100 mL). The combined organics were dried (Na2SO4), filtered and concentrated to give (S)-3-(tert-butoxycarbonyl(isopropyl)amino)-2-(5-chlorothiophen-2-yl)propanoic acid which was used in the next step without purification. MS (APCI+) [M+H] +348.2.

Workup

customthe reaction was quenched with 10% Na2SO3 (16 mL) at −5° C.
stirringstirred at room temperature for 30 minutes
customThe THF was removed in vacuo
extractionextracted with DCM (3×100 mL)
dry with materialThe combined organics were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-e82a8786355f4eb387913269948067ad
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359340B2

Reaction notes

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