Acetic-formic anhydride → HCID 86756429, compound
Reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C@@H:9]([CH2:18][CH2:19][CH3:20])[C@@H:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11]([OH:13])=[O:12].[C:21](OC=O)(=[O:23])C>N1C=CC=CC=1>[CH:21]([N:8]([O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[C@@H:9]([CH2:18][CH2:19][CH3:20])[C@@H:10]([CH2:14][CH:15]([CH3:16])[CH3:17])[C:11]([OH:13])=[O:12])=[O:23]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of (2R,3S)-3-(2-tetrahydropyranyloxyamino)-2-(2-methyl-1-propyl)hexanoic acid (7.90 g, 27.5 mmol) in 100 mL of anhydrous pyridine is cooled to 0° C. and treated with formic acetic anhydride (4.0 mL, 46 mmol). The reaction mixture is allowed to warm to 25° C., stirred for 6 h, and then concentrated to dryness under reduced pressure. The resulting gum is dissolved in 150 mL of EtOAc and washed successively with two 50-mL portions of 1 M aqueous sodium bisulfate and two 50-mL portions of saturated aqueous sodium chloride. The combined organic extracts are dried over sodium sulfate and filtered, and the solvents are removed under reduced pressure affording 8.67 g (99%) of (2R,3S)-3-(formyl-2-tetrahydropyranyloxyamino)-2-(2-methyl-1-propyl)hexanoic acid obtained as a viscous oil.
Workup
- concentrationconcentrated to dryness under reduced pressure
- dissolutionThe resulting gum is dissolved in 150 mL of EtOAc
- washwashed successively with two 50-mL portions of 1 M aqueous sodium bisulfate and two 50-mL portions of saturated aqueous sodium chloride
- dry with materialThe combined organic extracts are dried over sodium sulfate
- filtrationfiltered
- customthe solvents are removed under reduced pressure
Sources & evidence
- ORD record
- ord-fe1745be5e9a46689b068e9dc15ede28
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06191150B1
Reaction notes
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