Cesium carbonate → Benzyl 4-(2,3-dihydroxypropylthio)-2-methylbutan-2-ylcarbamate

HRID 1770699Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of benzyl 4-mercapto-2-methylbutan-2-ylcarbamate (17.4 g, 68.7 mmol) in N,N-dimethylformamide (200 ml) was added glycidol (5.0 ml, 75 mmol) and cesium carbonate (1.55 g, 4.76 mmol). The suspension was heated to 70° C. for 17 hours, then cooled to room temperature and concentrated in vacuo. The residue was purified by flash chromatography (20% to 100% ethyl acetate in hexanes) to afford the title compound as a clear oil (13.48 g, 41.17 mmol, 60%). 1H NMR (400 MHz, CDCl3) δ 1.30 (m, 6H), 2.0-2.1 (m, 2H), 2.24 (m, 1H), 2.49-2.62 (m, 3H), 2.71 (m, 1H), 3.5 (m, 1H), 3.7 (m, 2H), 4.75 (s, 1H), 5.06 (s, 2H), 7.3-7.4 (m, 5H); LRMS (ESI/APCI) m/z 328 [M+H]+, 350 [M+Na]+.

Workup

temperaturecooled to room temperature
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (20% to 100% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-08dd416cfad74d11ad0c5f74db07a74d
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09248117B2

Reaction notes

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