Dichloromethane → 1-{(4S,5R)-5-[4-(6-Chloromethyl-pyridin-3-yl)-phenyl]-4-fluoromethyl-2,2-dimethyl-oxazolidin-3-yl}-2,2-difluoro-ethanone

HRID 1520566ノート

反応式

[F:1][CH:2]([F:28])[C:3]([N:5]1[C@H:9]([CH2:10][F:11])[C@@H:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19](C)=[N:20][C:21](O)=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)[O:7][C:6]1([CH3:27])[CH3:26])=[O:4].C(N(CC)CC)C.CS(Cl)(=O)=O.[CH2:41]([Cl:43])Cl>>[Cl:43][CH2:41][C:21]1[N:20]=[CH:19][C:18]([C:15]2[CH:16]=[CH:17][C:12]([C@H:8]3[O:7][C:6]([CH3:26])([CH3:27])[N:5]([C:3](=[O:4])[CH:2]([F:28])[F:1])[C@@H:9]3[CH2:10][F:11])=[CH:13][CH:14]=2)=[CH:23][CH:22]=1

参加物

反応物 4

HCID 6344Dichloromethane

HCID 8471Triethylamine

HCID 31297Methanesulfonyl chloride

HCID 1784334402,2-Difluoro-1-{(4S,5R)-4-fluoromethyl-5-[4-(6-hydroxy-methyl-pyridin-3-yl)-phenyl]-2,2-dimethyl-oxazolidin-3-yl}-ethanone

生成物 1

HCID 866955331-{(4S,5R)-5-[4-(6-Chloromethyl-pyridin-3-yl)-phenyl]-4-fluoromethyl-2,2-dimethyl-oxazolidin-3-yl}-2,2-difluoro-ethanone

実験手順

A stirred solution of 2,2-Difluoro-1-{(4S,5R)-4-fluoromethyl-5-[4-(6-hydroxy-methyl-pyridin-3-yl)-phenyl]-2,2-dimethyl-oxazolidin-3-yl}-ethanone (1660 mg, 4.2 mmol) and triethylamine (0.88 ml, 6.31 mmol) in CH2Cl2 (30 ml) is treated with methanesulfonyl chloride (0.49 ml, 6.31 mmol) and stirred at ambient temperature for 16 hours. The reaction mixture is concentrated to dryness to afford the title compound as a red oil (1.53 g): 1H NMR (400 MHz, CDCl3) 1.60-1.77 (m, 6H), 4.53-4.84 (m, 5H), 5.25-5.31 (m, 1H), 6.12 (t, 1H), 7.58 (d, 2H), 7.65 (d, 2H), 7.68 (d, 1H), 8.03-8.07 (m, 1H), 8.86-8.90 (m, 1H). m/z M+H 413.

後処理

concentrationThe reaction mixture is concentrated to dryness

出典と根拠

ORDレコード: ord-287877b5025345c495fd5d146cc76562
出典データセット: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US09073894B2

反応ノート

読み込み中…