Ethyl Acetate → 2-benzyloxy-N-methyl-N-(3-methyl-2-oxobutyl)acetamide

HRID 1857716Notes

Reaction equation

[CH3:1][CH:2]([CH3:8])[C:3](=[O:7])[CH2:4][NH:5][CH3:6].C(OCC)(=O)C.C(=O)([O-])O.[Na+].[CH2:20]([O:27][CH2:28][C:29](Cl)=[O:30])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O>[CH2:20]([O:27][CH2:28][C:29]([N:5]([CH3:6])[CH2:4][C:3](=[O:7])[CH:2]([CH3:8])[CH3:1])=[O:30])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 6.1 g (52.9 mmol) of 3-methyl-1-methylamino-2-butanone, 70.0 ml of ethyl acetate and 41.0 ml of water was stirred at 0° C. Added was 7.1 g (84.6 mmol) of sodium hydrogen carbonate, and the mixture was stirred for 10 minutes. There was added 8.5 ml (54.0 mmol) of benzyloxyacetylchloride over 30 minutes. After stirring at room temperature for 10 hours, the ethyl acetate layer was seperated, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel chromatography (hexane/ethyl acetate 1:1) to give 5.8 g of 2-benzyloxy-N-methyl-N-(3-methyl-2-oxobutyl)-acetamide (18a') (yield 42%).

Workup

additionAdded
stirringthe mixture was stirred for 10 minutes
stirringAfter stirring at room temperature for 10 hours
customthe ethyl acetate layer was seperated
washwashed with saturated brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by silica gel chromatography (hexane/ethyl acetate 1:1)

Sources & evidence

ORD record: ord-90bd613fa49943bfbe4bf0929ac19370
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06147097

Reaction notes

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