Methanesulfonic Acid → N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4,6-difluorophenyl]-N'-(1-benzyl-4-piperidyl)urea methanesulfonate

HRID 53851Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([CH:35]=[C:36]([C:39]([CH3:42])([CH3:41])[CH3:40])[C:37]=1[OH:38])[CH2:8][CH2:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[C:11]=1[NH:18][C:19]([NH:21][CH:22]1[CH2:27][CH2:26][N:25]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:24][CH2:23]1)=[O:20])([CH3:4])([CH3:3])[CH3:2].[CH3:43][S:44]([OH:47])(=[O:46])=[O:45]>C(O)C>[CH3:43][S:44]([OH:47])(=[O:46])=[O:45].[C:39]([C:36]1[CH:35]=[C:7]([CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:37]=1[OH:38])[CH2:8][CH2:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[C:11]=1[NH:18][C:19]([NH:21][CH:22]1[CH2:27][CH2:26][N:25]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:24][CH2:23]1)=[O:20])([CH3:42])([CH3:41])[CH3:40]

Participants

Conditions

Temperature: 50 °C

Procedure

N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4,6-difluorophenyl]-N'-(1-benzyl-4-piperidyl)urea (0.50 g) was suspended in ethanol (10 ml) and heated at 50° C. to dissolve it. To the solution was added methanesulfonic acid (56 μl) and this solution was concentrated. The concentrate was dissolved with a mixed solvent of ethyl acetate (1 ml) and diisopropylether (3 ml). The solution was cooled to 0°-5° C. and allowed to stand overnight. The resultant crystals were filtered and dried to give the title compound (0.51 g, 87%).

Workup

dissolutionto dissolve it
concentrationthis solution was concentrated
dissolutionThe concentrate was dissolved with a mixed solvent of ethyl acetate (1 ml) and diisopropylether (3 ml)
temperatureThe solution was cooled to 0°-5° C.
filtrationThe resultant crystals were filtered
customdried

Sources & evidence

ORD record: ord-40cacb805f8d48449546279bd273b9ae
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05621010

Reaction notes

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