Acetic Acid → 1-[(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]propyl acetate

HRID 60714노트

반응식

HRID 60714 반응식
[C:1]([O:4][CH:5]([C@H:8]1[O:12][C@@H:11]([N:13]2[C:17]3[N:18]=[C:19]([NH2:23])[NH:20][C:21](=[O:22])[C:16]=3[S:15][C:14]2=[O:24])[C@@H:10](CC([O-])=O)[CH2:9]1)[CH2:6][CH3:7])(=[O:3])[CH3:2].C([O-])([O-])=[O:30].[K+].[K+].CC(O)=O>CO>[C:1]([O:4][CH:5]([C@@H:8]1[CH2:9][C@@H:10]([OH:30])[C@H:11]([N:13]2[C:17]3[N:18]=[C:19]([NH2:23])[NH:20][C:21](=[O:22])[C:16]=3[S:15][C:14]2=[O:24])[O:12]1)[CH2:6][CH3:7])(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 137190218[(2R,3R,5S)-5-(1-acetoxypropyl)-2-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)tetrahydrofuran-3-yl]acetate2회

생성물 1

HCID 1371086961-[(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]propyl acetate수율 88.9%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of [(2R,3R,5S)-5-(1-acetoxypropyl)-2-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)tetrahydrofuran-3-yl]acetate (compound 1g, 7.0 g, 16.9 mmol) in methanol (200 mL) was added K2CO3 (1.18 g, 8.5 mmol). After being stirred at room temperature for 12 hours, the reaction mixture was adjusted to pH 6.0 by addition of HOAc (1.2 g, 17 mmol), concentrated in vacuo and the residue was purified by column chromatography on silica gel (eluting with 1:2 EtOAc in petroleum ether) to afford 2.8 g of 1-[(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]propyl acetate (compound 22a) as a yellow solid. MS obsd. (ESI−) [(M−H)+]: 369.

후처리

  1. concentrationconcentrated in vacuo
  2. customthe residue was purified by column chromatography on silica gel (eluting with 1:2 EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-359a9a305e074d8d93f6e7265ee1aca4
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09441008B2

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