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

HRID 473460Notes

Reaction equation

HRID 473460 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[CH:33]=[CH:32][C:12]2[C:13](=[O:31])[C:14]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][C@H:24]4[CH2:28][O:27]C(C)(C)[O:25]4)=[CH:18][C:15]=3[CH2:16][CH2:17][C:11]=2[CH:10]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.O>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[CH:33]=[CH:32][C:12]2[C:13](=[O:31])[C:14]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][C@H:24]([OH:25])[CH2:28][OH:27])=[CH:18][C:15]=3[CH2:16][CH2:17][C:11]=2[CH:10]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 45280586(S)-2-(2-Aminophenylamino)-8-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-10,11-dihydrodibenzo[a,d]cyclohepten-5-one

Product 1

HCID 45280587(R)-2-(2-Aminophenylamino)-8-(2,3-dihydroxypropoxy)-10,11-dihydrodibenzo[a,d]cyclohepten-5-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

For the synthesis of the title compound, 0.10 g (0.225 mmol) of (S)-2-(2-amino-phenylamino)-8-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-10,11-dihydrodibenzo[a,d]cyclohepten-5-one and 0.0537 g (0.282 mmol) of p-toluenesulfonic acid monohydrate in 6 ml of methanol and 1.5 ml of water are reacted by method N. C24H24N2O4 (Mr=404.47)

Sources & evidence

ORD record
ord-23661f54e4bf4572b81f7e95c9f7c6a2
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

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