1,1'-Carbonyldiimidazole → HCID 86614043, compound

HRID 1727219Notes

Reaction equation

HRID 1727219 reaction equation
[Cl:1][C:2]1[C:11]2[N:10]([CH3:12])[O:9][C@H:8]3[NH:13][C@H:14]([C:16]([O:18][C@@H:19]4[C@:28]5([OH:29])[C@@H:23]([C@H:24]([CH:31]([CH3:34])[CH2:32][OH:33])[CH2:25][CH2:26][C@H:27]5[CH3:30])[CH:22]=[C:21]([CH3:35])[C@H:20]4[O:36][C:37](=[O:39])[CH3:38])=[O:17])[CH2:15][C@@:7]3([OH:40])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:41](N1C=CN=C1)([N:43]1[CH:47]=[CH:46][N:45]=[CH:44]1)=[O:42]>ClCCl.O>[Cl:1][C:2]1[C:11]2[N:10]([CH3:12])[O:9][C@H:8]3[NH:13][C@H:14]([C:16]([O:18][C@@H:19]4[C@:28]5([OH:29])[C@@H:23]([C@H:24]([CH:31]([CH3:34])[CH2:32][O:33][C:41]([N:43]6[CH:47]=[CH:46][N:45]=[CH:44]6)=[O:42])[CH2:25][CH2:26][C@H:27]5[CH3:30])[CH:22]=[C:21]([CH3:35])[C@H:20]4[O:36][C:37](=[O:39])[CH3:38])=[O:17])[CH2:15][C@@:7]3([OH:40])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 86614039HCID 86614039, compound

Product 1

HCID 86614043HCID 86614043, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To (1S,2R,4aS,5S,8R,8aR)-2-(acetyloxy)-8a-hydroxy-5-[2-hydroxy-1-methylethyl]-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl (2S,3aR,9bR)-6-chloro-9b-hydroxy-5-methyl-1,2,3,3a,5,9b-hexahydropyrrolo[2,3-c][2,1]benzoxazine-2-carboxylate(Preparation 140, 0.30 g, 0.52 mmol) in dichloromethane was added 1,1′-carbonyldiimidazole (0.92 g, 0.57 mmol) and the reaction mixture was stirred for 18 h. The reaction mixture was diluted with water and extracted with dichloromethane. The organic extracts were washed with brine, dried and then concentrated in vacuo. The crude product was purified by flash chromatography eluting with ethyl acetate:hexane (2:1) to give the title compound (0.16 g, 46%).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic extracts were washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography
  6. washeluting with ethyl acetate:hexane (2:1)

Sources & evidence

ORD record
ord-b8eb7a566a5b4e8eb10af64ce31da815
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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