Cesium carbonate → Benzyl 4-(2-(2-(2-hydroxyethoxy)ethoxy)ethylthio)-2-methylbutan-2-ylcarbamate

HRID 1770692Notes

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].Cl[CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][OH:27].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[OH:27][CH2:26][CH2:25][O:24][CH2:23][CH2:22][O:21][CH2:20][CH2:19][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 (6.70 g, 26.4 mmol) in N,N-dimethylformamide (100 ml) was added 2-(2-(2-chloroethoxy)ethoxy)ethanol (4.0 ml, 28 mmol) and cesium carbonate (8.06 g, 24.7 mmol). The suspension was heated to 70° C. for 17 hours, 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 (3.32 g, 8.61 mmol, 33%). 1H NMR (CDCl3, 400 MHz) δ 1.31 (s, 6H), 1.95-1.99 (m, 2H), 2.51-2.56 (m, 3H), 2.71 (t, J=5.6 Hz, 2H), 3.55-3.79 (m, 10H), 4.85 (s, 1H), 5.05 (s, 2H), 7.2-7.4 (m, 5H); LRMS (ESI/APCI) m/z 386 [M+H]+, 408 [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-58f529c4f4fd4696ab633f831746d77c
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09248117B2

Reaction notes

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