Acetic Anhydride → HCID 86614038, compound

HRID 1727164Notes

Reaction equation

HRID 1727164 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](OC(=O)C)(=[O:43])[CH3:42]>ClCCl.CN(C)C1C=CN=CC=1>[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](=[O:43])[CH3:42])[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 7918Acetic AnhydrideHCID 86614039HCID 86614039, compound

Product 1

HCID 86614038HCID 86614038, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

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, 63.8 mg, 0.11 mmol) in dichloromethane (1.1 ml) was added acetic anhydride (22 mg, 2.0 □l, 0.22 mmol) and 4-dimethylaminopyridine (14.3 mg, 0.12 mmol) and the reaction mixture stirred at room temperature for 18 hours. The reaction mixture was diluted with dichloromethane (20 ml) and washed with aqueous citric acid solution, dried (MgSO4) and concentrated in vacuo to give a gum. The crude product was purified by chromatography on silica eluting with hexane:ethyl acetate (60:40). The pure fractions were combined and concentrated in vacuo, to give the title product as a white solid (42 mg, 61%).

Workup

  1. washwashed with aqueous citric acid solution
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto give a gum
  5. customThe crude product was purified by chromatography on silica eluting with hexane:ethyl acetate (60:40)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4af60d4e0ef3436abb9d2941968103dc
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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