Dimethyl Sulfoxide → (S)-N-((1-(biphenylcarbonyl)-4-oxopyrrolidin-2-yl)methyl)quinoline-8-carboxamide

HRID 60788Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:12]([C:17]([N:19]2[CH2:23][C@H:22]([OH:24])[CH2:21][C@H:20]2[CH2:25][NH:26][C:27]([C:29]2[CH:30]=[CH:31][CH:32]=[C:33]3[C:38]=2[N:37]=[CH:36][CH:35]=[CH:34]3)=[O:28])=[O:18])=[CH:13][CH:14]=[CH:15][CH:16]=1.CCN(CC)CC>C(Cl)Cl>[C:11]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:12]([C:17]([N:19]2[CH2:23][C:22](=[O:24])[CH2:21][C@H:20]2[CH2:25][NH:26][C:27]([C:29]2[CH:30]=[CH:31][CH:32]=[C:33]3[C:38]=2[N:37]=[CH:36][CH:35]=[CH:34]3)=[O:28])=[O:18])=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of oxalyl chloride (39 μL, 0.45 mmol) in DCM (7 mL) at −78° C., was added a solution of DMSO (64 μL, 0.90 mmol) in DCM (4 mL). After stirring at −78° C. for 15 min, a solution of N-(((2S,4R)-1-(biphenylcarbonyl)-4-hydroxypyrrolidin-2-yl)methyl)quinoline-8-carboxamide (0.135 g, 0.30 mmol) in DCM (4 mL) was added. The resulting mixture was stirred at −78° C. for 1 h, treated with Et3N (0.25 mL, 1.8 mmol) dropwise and then allowed to warm to rt gradually over 1.5 h. The mixture was then concentrated in vacuo to a beige solid and purified by column chromatography on silica gel (70% MeOH in EtOAc) to provide (S)—N-((1-(biphenylcarbonyl)-4-oxopyrrolidin-2-yl)methyl)quinoline-8-carboxamide as a white solid (0.071 g, 53% yield). MS (ESI) 450.12 (M+H).

Workup

stirringThe resulting mixture was stirred at −78° C. for 1 h
temperatureto warm to rt gradually over 1.5 h
concentrationThe mixture was then concentrated in vacuo to a beige solid
custompurified by column chromatography on silica gel (70% MeOH in EtOAc)

Sources & evidence

ORD record: ord-5f4087b19e5849aab8b0efd53b11e27a
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440982B2

Reaction notes

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