Potassium Hydroxide → HCID 67508690, compound

HRID 1770686Notes

Reaction equation

[OH:1][CH:2]([CH:21]1[CH2:23][O:22]1)[CH2:3][S:4][CH2:5][CH2:6][C:7]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:9])[CH3:8].[OH-:24].[K+]>CS(C)=O.O.C(OCC)(=O)C>[CH3:9][C:7]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([CH2:6][CH2:5][S:4][CH2:3][CH:2]([OH:1])[CH:21]([OH:24])[CH2:23][OH:22])[CH3:8]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of benzyl 4-(2-hydroxy-2-(oxiran-2-yl)ethylthio)-2-methylbutan-2-ylcarbamate (3.33 g, 9.81 mmol) in dimethylsulfoxide (50 ml) and H2O (10 ml) was added 5.0 M KOH (600 μl, 3.0 mmol). The solution was heated to 90° C. for 5 hour, cooled to room temperature, diluted with 400 ml ethyl acetate, washed with 1×200 ml 5% NaHSO4, 5×200 ml saturated NaCl, dried on MgSO4, and concentrated in vacuo. The residue was purified by preparatory HPLC (H2O/acetonitrile) to give the title compound as a clear oil (159.3 mg, 0.446 mmol, 45%) as a mixture of diastereomers. 1H NMR (400 MHz, CDCl3) δ 1.28 (s, 6H), 1.9-2.1 (m, 2H), 2.50 (m, 2H), 2.6-2.7 (m, 2H), 3.6-3.8 (m, 4H), 3.85 (br s, 3H), 4.93 (s, 1H), 5.04 (s, 2H), 7.3-7.4 (m, 5H); LRMS (ESI/APCI) m/z 358 [M+H]+, 380 [M+Na]+.

Workup

temperaturecooled to room temperature
washwashed with 1×200 ml 5% NaHSO4, 5×200 ml saturated NaCl
customdried on MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by preparatory HPLC (H2O/acetonitrile)

Sources & evidence

ORD record: ord-69cf0e15e2b4465f9e1ba2b7cbb6b818
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09248117B2

Reaction notes

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