p-Toluenesulfonic acid monohydrate → (R)-8-(2,4-Difluorophenylamino)-1-(2,3-dihydroxypropoxy)-10,11-dihydrodibenzo-[a,d]cyclohepten-5-one

HRID 473473Notes

Reaction equation

HRID 473473 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:11]=[CH:12][C:13]2[C:19](=[O:20])[C:18]3[CH:21]=[CH:22][CH:23]=[C:24]([O:25][CH2:26][C@H:27]4[CH2:31][O:30]C(C)(C)[O:28]4)[C:17]=3[CH2:16][CH2:15][C:14]=2[CH:34]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:11]=[CH:12][C:13]2[C:19](=[O:20])[C:18]3[CH:21]=[CH:22][CH:23]=[C:24]([O:25][CH2:26][C@H:27]([OH:28])[CH2:31][OH:30])[C:17]=3[CH2:16][CH2:15][C:14]=2[CH:34]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 45280642HCID 45280642, compound

Product 1

HCID 45280643(R)-8-(2,4-Difluorophenylamino)-1-(2,3-dihydroxypropoxy)-10,11-dihydrodibenzo-[a,d]cyclohepten-5-oneYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

For the synthesis of the title compound, 0.10 g (0.215 mmol) of (S)-8-(2,4-difluorophenylamino)-1-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-10,11-dihydrodibenzo[a,d]cyclohepten-5-one and 0.0054 g (0.0284 mmol) of p-toluenesulfonic acid monohydrate in 6 ml of methanol and 1.5 ml of water are reacted by method N. Yield: 88%;

Sources & evidence

ORD record
ord-5064c6165c6e493e9647e32d37a8ab16
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

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