Acetic Anhydride → (2R,3S,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-5-(difluoromethyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl acetate

HRID 2205185ノート

反応式

HRID 2205185 の反応式
[CH3:1][C:2](OC(C)=O)=[O:3].[CH2:8]([O:15][C@@H:16]1[C@:20]([CH2:24][O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([CH:21]([F:23])[F:22])[O:19][C@@H:18]([N:33]2[CH:38]=[CH:37][C:36](=[O:39])[NH:35][C:34]2=[O:40])[C@H:17]1[OH:41])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1C=CC=CC=1>[C:2]([O:41][C@H:17]1[C@H:16]([O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@:20]([CH2:24][O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([CH:21]([F:22])[F:23])[O:19][C@H:18]1[N:33]1[CH:38]=[CH:37][C:36](=[O:39])[NH:35][C:34]1=[O:40])(=[O:3])[CH3:1]

参加物

4

反応物 2

HCID 7918Acetic AnhydrideHCID 1182943391-((2R,3S,4S,5R)-4-(Benzyloxy)-5-((benzyloxy)methyl)-5-(difluoromethyl)-3-hydroxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

生成物 1

HCID 118294157(2R,3S,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-5-(difluoromethyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl acetate収率 88%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
20 °C

実験手順

Ac2O (0.5 mL) was added into a solution of compound 34 (0.114 g, 0.24 mmol) in dry pyridine (4 mL). The reaction mixture was stirred at 20° C. for 3 h and then quenched by saturated aqueous NaHCO3 solution (2 mL). The organic phase was extracted with dichloromethane and then evaporated to dryness under reduced pressure. Purification by silica gel chromatography [petroleum ether:ethyl acetate (4:1)] afforded 35 (0.12 g, 88%) as a white solid. LC-MS: (M+H)+=517.2

後処理

  1. customquenched by saturated aqueous NaHCO3 solution (2 mL)
  2. extractionThe organic phase was extracted with dichloromethane
  3. customevaporated to dryness under reduced pressure
  4. customPurification by silica gel chromatography [petroleum ether:ethyl acetate (4:1)]

出典と根拠

ORDレコード
ord-171eb1c8264748cfa0a082b7d911659e
出典データセット
uspto-grants-2016_06
特許番号
US09370569B2

反応ノート

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