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

HRID 1397527Notes

Reaction equation

HRID 1397527 reaction equation
[OH:1][C@@H:2]1[C@@H:6]2[O:7][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[O:9][CH2:10][C@@H:5]2[CH2:4][C@H:3]1[N:19]1[C:27](=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]1=[O:29].[CH:30]1[CH:35]=[CH:34][C:33]([O:36][C:37](Cl)=[S:38])=[CH:32][CH:31]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:37](=[S:38])([O:36][C:33]1[CH:34]=[CH:35][CH:30]=[CH:31][CH:32]=1)[O:1][C@@H:2]1[C@@H:6]2[O:7][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[O:9][CH2:10][C@@H:5]2[CH2:4][C@H:3]1[N:19]1[C:20](=[O:29])[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:27]1=[O:28]

Participants

5

Reactant 2

HCID 70498Phenyl thioxochloroformateHCID 596713592-[(4As,6r,7s,7ar)-7-hydroxy-2-(4-methoxyphenyl)-hexahydrocyclopenta[d][1,3]dioxin-6-yl]-1h-isoindole-1,3(2h)-dione

Product 1

HCID 59671288O-[(4aS,6R,7S,7aR)-6-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-(4-methoxyphenyl)hexahydrocyclopenta[d][1,3]dioxin-7-yl] O-phenyl thiocarbonateYield 97%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-[(4aS,6R,7S,7aR)-7-hydroxy-2-(4-methoxyphenyl)-hexahydrocyclopenta[d][1,3]dioxin-6-yl]-1H-isoindole-1,3(2H)-dione (1.26 g, 3.19 mmol) in DCM (150. mL) was added DMAP (1.17 g, 9.54 mmol) and phenyl chlorothionoformate (0.661 mL, 4.78 mmol) under an atmosphere of argon. After 2 h, the mixture was concentrated in vacuo and the residue was purified via silica gel chromatography eluting with a gradient of 0 to 5% EtOAc in DCM to afford the title compound as a white amorphous solid (1.64 g, 97%). LC/MS: Rt=2.21 min, ES+ 532 (AA standard).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue was purified via silica gel chromatography
  3. washeluting with a gradient of 0 to 5% EtOAc in DCM

Sources & evidence

ORD record
ord-27be2aa0c9194e6bb08ad24bafd8f994
Source dataset
uspto-grants-2014_12
Patent number
US08901136B2

Reaction notes

Loading…