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

Reaktionsgleichung

Reaktionsgleichung von HRID 222155
[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

Komponenten

5

Edukt 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

Produkt 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 thiocarbonateAusbeute 140 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f8505db5cd444e14906936723e0e1573
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207177B2

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