Triethylamine → Cyclohexylcarbamic acid 4-hydroxymethyl-5-oxo-2,3,4,5-tetrahydro-benzo[b]thiepin-4-ylmethyl ester

HRID 2265818Notes

Reaction equation

[OH:1][CH2:2][C:3]1([CH2:15][OH:16])[CH2:9][CH2:8][S:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[C:4]1=[O:14].C(N(CC)CC)C.[CH:24]1([N:30]=[C:31]=[O:32])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>O1CCCC1>[OH:16][CH2:15][C:3]1([CH2:2][O:1][C:31](=[O:32])[NH:30][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:9][CH2:8][S:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[C:4]1=[O:14]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4,4-bis(hydroxymethyl)-3,4-dihydro-2H-benzo[b]thiepin-5-one (424 mg, 1.78 mmol) in 22 ml of tetrahydrofuran were added, at 0° C., triethylamine (0.27 ml, 1.96 mmol) and cyclohexyl isocyanate (1.0 ml, 7.84 mmol). The mixture was stirred at 80° C. for 18 hours, concentrated and purified by column chromatography on silica (eluent: 1:2 tert-butyl methyl ether/cyclohexane). The product was obtained in a yield of 366 mg (57%).

Workup

concentrationconcentrated
custompurified by column chromatography on silica (eluent: 1:2 tert-butyl methyl ether/cyclohexane)
customThe product was obtained in a yield of 366 mg (57%)

Sources & evidence

ORD record: ord-6a41d4fdb8d249198f536134a98c21ff
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858613B2

Reaction notes

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