Formic Acid → HCID 57833600, compound
Reaction equation
C(OC(=O)C)(=O)C.[CH:8]([OH:10])=O.[NH2:11][C:12]1[C:25]2[O:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[C:26]3[CH2:32][CH:31]4[N:33]([C:34](=[O:39])[C:35]([F:38])([F:37])[F:36])[CH:28]([CH2:29][CH2:30]4)[CH2:27]3)[C:16]=2[CH:15]=[CH:14][CH:13]=1>C1COCC1.C(Cl)Cl>[F:38][C:35]([F:36])([F:37])[C:34]([N:33]1[CH:31]2[CH2:30][CH2:29][CH:28]1[CH2:27][C:26](=[C:17]1[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([NH:11][CH:8]=[O:10])[C:25]=3[O:24][C:23]3[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:32]2)=[O:39]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
Into a flask was placed acetic anhydride (4 mL) and the reaction was cooled in an ice bath. Upon cooling, formic acid (2 mL) was added and the mixture was heated to 50° C. for 15 min, and then cooled to rt. Upon cooling, the resulting solution (0.6 mL) was added to an ice bath-cooled solution of compound 4k (0.300 g, 6.0 mmol) in THF (2 mL), and the reaction was heated to 50° C. for 1 h. The mixture was cooled to rt, diluted with methylene chloride, and the organic phase was washed sequentially with saturated aqueous sodium bicarbonate solution and brine. The organic phase was dried over MgSO4, filtered, and concentrated to yield 0.42 g of the title compound 5k.
Workup
- customInto a flask was placed
- temperatureUpon cooling
- temperaturecooled to rt
- temperatureUpon cooling
- temperaturethe reaction was heated to 50° C. for 1 h
- temperatureThe mixture was cooled to rt
- washthe organic phase was washed sequentially with saturated aqueous sodium bicarbonate solution and brine
- dry with materialThe organic phase was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-149b788f4ba7409e97c1c365ab917674
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582650B2
Reaction notes
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