Triethylamine → HCID 178467443, compound

HRID 928107Notes

Reaction equation

[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)([OH:10])[CH3:9])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl.O.C(=O)(O)[O-].[Na+]>[OH:10][C:8]([C@H:5]1[CH2:6][CH2:7][C@H:2]([NH:1][S:24]([CH3:23])(=[O:26])=[O:25])[CH2:3][CH2:4]1)([C:11]1[S:12][CH:13]=[CH:14][N:15]=1)[CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-(trans-4-aminocyclohexyl)-1-(1,3-thiazol-2-yl)ethanol (100 mg, 0.44 mmol) in dichlormethane (2.9 mL) and triethylamine (0.31 mL, 2.21 mmol) at 0° C. was added methanesulfonyl chloride (34 μL, 0.44 mmol) and the reaction was allowed to stir for 10 minutes at 0° C. and then diluted with water, dichloromethane and aqueous saturated sodium bicarbonate. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (0-100% ethyl acetate gradient in hexanes) to afford N-{trans-4-[1-hydroxy-1-(1,3-thiazol-2-yl)ethyl]cyclohexyl}methanesulfonamide. MS ESI calc'd. for C12H21N2O3S2 [M+H]+ 305. found 305. 1H NMR (500 MHz, CDCl3) δ 7.70 (d, J=3.2, 1H), 7.28 (d, J=3.2, 1H), 4.25-4.14 (m, 1H), 3.30-3.13 (m, 1H), 2.95 (s, 3H), 2.18-2.09 (m, 1H), 2.09-2.02 (m, 2H), 1.96-1.88 (m, 1H), 1.80-1.69 (m, 1H), 1.64-1.53 (m, 3H), 1.40-1.28 (m, 1H), 1.28-1.13 (m, 3H).

Workup

customThe organic layer was separated
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography on silica gel (0-100% ethyl acetate gradient in hexanes)

Sources & evidence

ORD record: ord-a28647c92bc2451383c888f6a3356267
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290490B2

Reaction notes

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