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 2205185노트

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HRID 2205185 반응식
[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]

참가 물질

4

반응물 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

생성물 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 acetate수율 88%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
20 °C

실험 절차

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

후처리

  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)]

출처 및 근거

ORD 기록
ord-171eb1c8264748cfa0a082b7d911659e
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09370569B2

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