Phenyl thioxochloroformate → O-[(4aS,6R,7S,7aR)-6-[4-(benzylsulfanyl)-7H-pyrrolo[2,3-d]-pyrimidin-7-yl]-2-(4-methoxyphenyl)hexahydrocyclopenta[d][1,3]dioxin-7-yl] O-phenyl thiocarbonate

HRID 222155

반응식

HRID 222155 반응식
[CH2:1]([S:8][C:9]1[C:10]2[CH:17]=[CH:16][N:15]([C@H:18]3[C@H:34]([OH:35])[C@@H:21]4[O:22][CH:23]([C:26]5[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=5)[O:24][CH2:25][C@@H:20]4[CH2:19]3)[C:11]=2[N:12]=[CH:13][N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:36]1[CH:41]=[CH:40][C:39]([O:42][C:43](Cl)=[S:44])=[CH:38][CH:37]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:43](=[S:44])([O:42][C:39]1[CH:40]=[CH:41][CH:36]=[CH:37][CH:38]=1)[O:35][C@@H:34]1[C@@H:21]2[O:22][CH:23]([C:26]3[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=3)[O:24][CH2:25][C@@H:20]2[CH2:19][C@H:18]1[N:15]1[C:11]2[N:12]=[CH:13][N:14]=[C:9]([S:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:10]=2[CH:17]=[CH:16]1

참가 물질

5

반응물 2

HCID 70498Phenyl thioxochloroformateHCID 66618376(4As,6r,7s,7ar)-6-[4-(benzylsulfanyl)-7h-pyrrolo[2,3-d]-pyrimidin-7-yl]-2-(4-methoxyphenyl)hexahydrocyclopenta[d][1,3]dioxin-7-ol

생성물 1

HCID 86614246O-[(4aS,6R,7S,7aR)-6-[4-(benzylsulfanyl)-7H-pyrrolo[2,3-d]-pyrimidin-7-yl]-2-(4-methoxyphenyl)hexahydrocyclopenta[d][1,3]dioxin-7-yl] O-phenyl thiocarbonate수율 140%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of (4aS,6R,7S,7aR)-6-[4-(benzylsulfanyl)-7H-pyrrolo[2,3-d]-pyrimidin-7-yl]-2-(4-methoxyphenyl)hexahydrocyclopenta[d][1,3]dioxin-7-ol (990. mg, 2.02 mmol) in DCM (57.0 mL) was added 4-(dimethylamino)-pyridine (748 mg, 6.07 mmol) and phenyl chlorothionocarbonate (0.565 mL, 4.04 mol) under an atmosphere of nitrogen and the yellow reaction was stirred at rt. After 12 h, the dark yellow solution was purified via silica gel chromatography eluting with 10% EtOAc in hexanes, and then 10% MeOH in DCM on a column pre-treated with 1% TEA in hexanes to afford the title compound as a yellow oil (1.77 g, 97%). LC/MS: Rt=2.47 min, ES+ 626 (FA standard).

후처리

  1. customthe yellow reaction
  2. customthe dark yellow solution was purified via silica gel chromatography
  3. washeluting with 10% EtOAc in hexanes
  4. addition10% MeOH in DCM on a column pre-treated with 1% TEA in hexanes

출처 및 근거

ORD 기록
ord-f8505db5cd444e14906936723e0e1573
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207177B2

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