Water → tert-butyl ((S)-3-cyclopentyl-1-((R)-oxiran-2-yl)-1-oxopropan-2-yl)carbamate

HRID 58842Notes

Reaction equation

[CH:1]1([CH2:6][C@H:7]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:8](=[O:11])[CH:9]=[CH2:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH2:20]>CN(C=O)C>[CH:1]1([CH2:6][C@H:7]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:8]([C@H:9]2[CH2:10][O:20]2)=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (S)-tert-butyl (1-cyclopentyl-3-oxopent-4-en-2-yl)carbamate (854 mg, 3.20 mmol) in DMF (70 mL) was cooled to −20° C. and a bleach solution (9.50 mL, 12.8 mmol, 10% active spice) was added dropwise under nitrogen. The reaction mixture was warmed to 0° C. and stirred for 1.5 h. Water (70 mL) was added and the mixture was extracted with EtOAc (2×50 mL). The organic phases were combined, washed with brine (2×50 mL), dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=80:1) to afford tert-butyl ((S)-3-cyclopentyl-1-((R)-oxiran-2-yl)-1-oxopropan-2-yl)carbamate as a viscous oil (390 mg, contaminated with some impurities, 43% yield) as a yellow oil.

Workup

additiona bleach solution (9.50 mL, 12.8 mmol, 10% active spice) was added dropwise under nitrogen
extractionthe mixture was extracted with EtOAc (2×50 mL)
washwashed with brine (2×50 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated
customThe residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=80:1)

Sources & evidence

ORD record: ord-b2c41de663604c36b20f465b180f50f0
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434761B2

Reaction notes

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