Ammonium Acetate → HCID 59331384, compound

HRID 1882010Notes

Reaction equation

[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10](/[C:13](=[CH:25]\[CH:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)/[C:14](=O)[CH2:15][CH2:16][C:17]([C:19]3[S:20][CH:21]=[CH:22][N:23]=3)=O)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C([O-])(=O)C.[NH4+:36]>C(O)(=O)C.C(OCC)(=O)C>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10](/[C:13](/[C:14]3[NH:36][C:17]([C:19]4[S:20][CH:21]=[CH:22][N:23]=4)=[CH:16][CH:15]=3)=[CH:25]\[CH:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)=[CH:11][CH:12]=2)(=[O:5])=[O:6])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of (5E)-5-[4-(cyclopropylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)-1-(1,3-thiazol-2-yl)hex-5-ene-1,4-dione (278 mg) in acetic acid (5 mL) was added ammonium acetate (750 mg), and the mixture was stirred at 110° C. for 45 min. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (133 mg, yield 50%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (3:2, volume ratio). MS: 441 (MH+).

Workup

temperatureAfter cooling to room temperature
washwashed with water
washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-6d7e7ed077794e01b9561c7cece1fecd
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318746B2

Reaction notes

Loading…