Acetic Anhydride → HCID 131726613, compound

HRID 1178301Notes

Reaction equation

HRID 1178301 reaction equation
[OH:1][C@@H:2]1[C:7]2=[C:8]3[C:17](=[C:18]([O:20][CH3:21])[CH:19]=[C:6]2[O:5][C:4]([CH3:29])([CH3:28])[C@@H:3]1[OH:30])[C:16](=[O:22])[C:15]1[C:10](=[CH:11][CH:12]=[C:13]2[CH:26]=[CH:25][CH:24]=[CH:23][C:14]2=1)[N:9]3[CH3:27].[C:31]1(=[O:37])[O:36][C:34](=[O:35])[CH2:33][CH2:32]1.CN(C1C=CC=CN=1)C.[C:47](OC(=O)C)(=[O:49])[CH3:48]>N1C=CC=CC=1>[C:47]([O:1][C@@H:2]1[C:7]2=[C:8]3[C:17](=[C:18]([O:20][CH3:21])[CH:19]=[C:6]2[O:5][C:4]([CH3:28])([CH3:29])[C@@H:3]1[O:30][CH:33]([CH2:32][CH:31]=[O:37])[C:34]([OH:36])=[O:35])[C:16](=[O:22])[C:15]1[C:10](=[CH:11][CH:12]=[C:13]2[CH:26]=[CH:25][CH:24]=[CH:23][C:14]2=1)[N:9]3[CH3:27])(=[O:49])[CH3:48]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 7922Succinic anhydrideHCID 218852-DimethylaminopyridineHCID 11697098HCID 11697098, compound

Product 1

HCID 131726613HCID 131726613, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 0.5 mmol of the compound of Example 4 in 3 ml of anhydrous pyridine there are added 1.1 equivalents of succinic anhydride and 1 mg of dimethylaminopyridine. Stir for 2 days in the dark and at ambient temperature, then add 25 ml of acetic anhydride at −15° C. and stir for 1.5 hours before concentrating under reduced pressure. Chromatography over silica gel (dichloromethane/acetic acid: 99/1) allows the expected product to be isolated.

Workup

  1. stirringstir for 1.5 hours
  2. concentrationbefore concentrating under reduced pressure
  3. customto be isolated

Sources & evidence

ORD record
ord-599b9c24997b43d59ce3db8276e07277
Source dataset
uspto-grants-2007_10
Patent number
US07276512B2

Reaction notes

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