Ammonia → HCID 178513944, compound

HRID 1984923Notes

Reaction equation

[F:1][C:2]([F:32])([F:31])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[CH:7][C:6]=1[S:17]([NH:20][CH2:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([C:28]([OH:30])=O)[CH2:24][CH2:23]1)(=[O:19])=[O:18].C([N:35](CC)CC)C.ClC(OCC)=O.N>C1COCC1>[F:32][C:2]([F:31])([F:1])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]([F:16])([F:14])[F:15])=[CH:7][C:6]=1[S:17]([NH:20][CH2:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([C:28]([NH2:35])=[O:30])[CH2:24][CH2:23]1)(=[O:18])=[O:19]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of trans-4-{[2,5-bis-(2,2,2-trifluoro-ethoxy)-benzenesulfonylamino]-methyl}-cyclohexanecarboxylic acid (2.78 g, 5.63 mmol) and triethylamine (1.9 mL, 13.6 mmol) in THF (25 mL) was cooled to 0° C. To the mixture was added ethyl chloroformate (0.586 mL, 6.2 mmol) in THF (5 mL) over 10 min. After stirring at 0° C. for 15 min, 25% aqueous ammonia (10 mL) was added dropwise. The mixture was stirred at ambient temperature for 2 hr. The resulting mixture was concentrated under reduced pressure and the concentrate was diluted with water to give a solid. The solid was filtered and washed with water and hexanes to give trans-4-{[2,5-bis-(2,2,2-trifluoro-ethoxy)-benzenesulfonylamino]-methyl}-cyclohexanecarboxylic acid amide as a white solid (2.7 g, 98%).

Workup

stirringThe mixture was stirred at ambient temperature for 2 hr
concentrationThe resulting mixture was concentrated under reduced pressure
additionthe concentrate was diluted with water
customto give a solid
filtrationThe solid was filtered
washwashed with water and hexanes

Sources & evidence

ORD record: ord-058cd83283dd4a6ea3d9ce4f0801929d
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544690B2

Reaction notes

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