Chloroacetone → HCID 57642030, compound

HRID 2112428Notes

Reaction equation

[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([C:17](=[O:19])[NH2:18])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:28][C:29](=[O:31])[CH3:30].S([O-])(O)(=O)=O.[Na+]>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([C:17](=[O:19])[NH2:18])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:28][C:29](=[O:31])[CH3:30])=[CH:14][CH:15]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of [(S)-1-carbamoyl-2-(4-hydroxyphenyl)ethyl]-carbamic acid tert-butyl ester (3.00 g, 10.7 mmol) and potassium carbonate (7.40 g, 53.5 mmol) in N,N-dimethylformamide (50 ml) were added subsequently chloroacetone (1.02 ml, 12.8 mmol) and tetrabutylammonium iodide (197 mg, 0.54 mmol). The reaction mixture was heated to 90° C. for 16 h and cooled to room temperature. It was diluted with water (100 ml) and acidified with a 10% solution of sodium hydrogensulphate to pH 2. Ethyl acetate (300 ml) was added. The phases were separated. The organic layer was washed with water (3×150 ml) and dried over magnesium sulphate. The solvent was removed in vacuo to give 2.65 g of {(S)-1-carbamoyl-2-[4-(2-oxopropoxy)phenyl]ethyl}carbamic acid tert-butyl ester.

Workup

temperaturecooled to room temperature
customThe phases were separated
washThe organic layer was washed with water (3×150 ml)
dry with materialdried over magnesium sulphate
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-dcb70f38c08f48089a7afbfce3d73e91
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07524813B2

Reaction notes

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