Ethanol → HCID 72191132, compound

HRID 1487051Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:28][CH:29]([CH3:31])[CH3:30])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:15][C:14]=1[OH:27])(=[O:12])=[O:11].[CH2:32](O)[CH3:33].C(P(CCCC)(CCCC)=CC#N)CCC>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:28][CH:29]([CH3:31])[CH3:30])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)=[CH:15][C:14]=1[O:27][CH2:32][CH3:33])(=[O:11])=[O:12]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of N-(2,4-dimethylphenyl)-2-hydroxy-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide (15.7 mg, 0.035 mmol) and ethanol (4.8 mg, 0.105 mmol) in toluene (1.5 mL) stirred in air at 20° C., was added a solution of 2-(tributylphosphoranylidene)acetonitrile (8.47 mg, 0.035 mmol) in toluene (0.5 mL) over 1 minute. The reaction mixture was stirred at 20° C. for 24 hours. Additional 2-(tributylphosphoranylidene)acetonitrile (8.47 mg, 0.035 mmol) was then added and the reaction stirred for a further 2 hours. The solvent was evaporated in vacuo and the residue purified by pre-packed silica cartridge eluting with ethyl acetate-cyclohexane (0-50%). The relevant fractions were evaporated to give the title product, 8.7 mg. LCMS [LCMS1] Rt 1.48 min, m/z (ES+) 476 (M+H).

Workup

stirringthe reaction stirred for a further 2 hours
customThe solvent was evaporated in vacuo
customthe residue purified by pre-packed silica cartridge
washeluting with ethyl acetate-cyclohexane (0-50%)
customThe relevant fractions were evaporated

Sources & evidence

ORD record: ord-baea17bfe3204a6a8b6490cbc436de63
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428452B2

Reaction notes

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