Methyl iodide → HCID 66857525, compound

HRID 2037528Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([N:17]2[CH2:22][CH2:21][C@:20]([CH2:30][CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[O:19][C:18]2=[O:40])[CH3:16])=[CH:11][CH:10]=1.[H-].[Na+].I[CH3:44]>O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([N:17]2[CH2:22][CH2:21][C@:20]([CH2:30][CH2:31][N:32]([CH3:44])[C:33](=[O:39])[O:34][C:35]([CH3:36])([CH3:38])[CH3:37])([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[O:19][C:18]2=[O:40])[CH3:16])=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl 2-((R)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethylcarbamate (53 mg, 0.1 mmol) in tetrahydrofuran was added NaH (300 mg, 12.5 mmol) at 0° C. The mixture was stirred at 0° C. for 1 h. Then iodomethane (1.3 g, 9.15 mmol) was added to the above mixture and the mixture was stirred for 2 h. The reaction was quenched with H2O and extracted with EtOAc to give the organic layer which was washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated to give tert-butyl 2-((R)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethyl(methyl)carbamate (36 mg, 66%).

Workup

stirringthe mixture was stirred for 2 h
customThe reaction was quenched with H2O
extractionextracted with EtOAc
customto give the organic layer which
washwas washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-54b80f55c3934c36a781dbff4b47db43
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575156B2

Reaction notes

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