Acetic Anhydride → HCID 69688847, compound

HRID 1266648Notes

Reaction equation

HRID 1266648 reaction equation
[CH3:1][O:2][CH:3]([O:40][CH3:41])[CH2:4][NH:5][C:6]([CH:8]([CH2:34][CH2:35][C:36]([OH:39])([CH3:38])[CH3:37])[CH2:9][CH:10]([OH:33])[CH:11]([NH:20][C:21]([C:23]1[CH:32]=[N:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=1)=[O:22])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)=[O:7].CN(C1C=CC=CN=1)C.[C:51](OC(=O)C)(=[O:53])[CH3:52]>N1C=CC=CC=1.C(Cl)Cl>[CH3:1][O:2][CH:3]([O:40][CH3:41])[CH2:4][NH:5][C:6]([CH:8]([CH2:34][CH2:35][C:36]([OH:39])([CH3:37])[CH3:38])[CH2:9][CH:10]([O:33][C:51](=[O:53])[CH3:52])[CH:11]([NH:20][C:21]([C:23]1[CH:32]=[N:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=1)=[O:22])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)=[O:7]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 86585879HCID 86585879, compound

Product 1

HCID 69688847HCID 69688847, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of quinoxaline-2-carboxylic acid [4-(2,2-dimethoxy-ethylcarbamoyl)-1-(3-fluoro-benzyl)-2,7-dihydroxy-7-methyl-octyl]-amide (192 mg, 0.336 mmol) in pyridine (0.6 mL) was added dimethylaminopyridine (DMAP) (10 mg, 0.082 mmol) and acetic anhydride (0.093 mL, 0.984 mmol). The resulting solution was stirred for 3 hours then diluted with methylene chloride and washed with 1 M hydrochloric acid. The organic layer was dried over sodium sulfate, filtered and concentrated to give the title compound as a white foam (198 mg, 96%).

Workup

  1. washwashed with 1 M hydrochloric acid
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-241066ed72d74d48808e0c863d1b1d90
Source dataset
uspto-grants-2003_04
Patent number
US06548671B2

Reaction notes

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