Dimethyl Sulfoxide → HCID 58468004, compound

HRID 1879390Notes

Reaction equation

CS(C)=O.C(Cl)(=O)C(Cl)=O.[F:11][C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=1[C@@H:19]1[CH2:29][CH2:28][C@@H:27]([OH:30])[C:22]2=[N:23][CH:24]=[CH:25][CH:26]=[C:21]2[C@H:20]1[NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35].C(N(CC)CC)C>C(Cl)Cl>[F:11][C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=1[C@@H:19]1[CH2:29][CH2:28][C:27](=[O:30])[C:22]2=[N:23][CH:24]=[CH:25][CH:26]=[C:21]2[C@H:20]1[NH:31][C:32](=[O:38])[O:33][C:34]([CH3:36])([CH3:35])[CH3:37]

Participants

Conditions

Temperature: -65 °C

Procedure

Dimethylsulfoxide (0.145 mL, 2.049 mmol) was added to a methylene chloride (10 mL) solution of oxalyl chloride (0.768 mL, 1.537 mmol) at −20° C. under nitrogen. The reaction was then cooled to −65° C. and tert-butyl (5S,6S,9R)-6-(2,3-difluorophenyl)-9-hydroxy-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate (0.2 g, 0.512 mmol) was added to the reaction all at once. The reaction was stirred for 2 h. Triethylamine (0.428 mL, 3.07 mmol) was added to the reaction mixture and the reaction was allowed to warm to room temperature. The reaction was diluted with methylene chloride and washed with water three times. The methylene chloride layer was separated, dried (sodium sulfate), filtered and concentrated. Flash chromatography using ethyl acetate in hexane from 0 to 45% to 65% gave the desired product (199 mg, 73%).

Workup

temperatureto warm to room temperature
washwashed with water three times
customThe methylene chloride layer was separated
dry with materialdried (sodium sulfate)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-f36990f8de204fee81e7df2cbf4ef0cd
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314117B2

Reaction notes

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