Methanol → HCID 86730244, compound

HRID 1850202Notes

Reaction equation

HRID 1850202 reaction equation
[CH3:1][C@:2]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:6][O:5][C:4](=[O:7])[N:3]1[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH:14][CH:15]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:19][CH:18]=2)[CH3:16])[N:9]=1.CO>C(=O)=O>[CH3:1][C@:2]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:6][O:5][C:4](=[O:7])[N:3]1[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C@H:15]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:19][CH:18]=2)[CH3:16])[N:9]=1.[CH3:1][C@:2]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:6][O:5][C:4](=[O:7])[N:3]1[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C@@H:15]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:19][CH:18]=2)[CH3:16])[N:9]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 86730246HCID 86730246, compound

Product 2

HCID 86730244HCID 86730244, compoundHCID 86730245HCID 86730245, compound

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

(4S)-4-methyl-4-phenyl-3-(2-(1-(4-(piperidin-1-yl)phenyl)ethylamino)pyrimidin-4-yl)oxazolidin-2-one (example 141, 51 mg) was resolved on a column (IA 4.6×100 mm) using 45% MeOH in CO2 to give (S)-4-methyl-4-phenyl-3-(2-((S)-1-(4-(piperidin-1-yl)phenyl)ethylamino)pyrimidin-4-yl)oxazolidin-2-one and (S)-4-methyl-4-phenyl-3-(2-((R)-1-(4-(piperidin-1-yl)phenyl)ethylamino)pyrimidin-4-yl)oxazolidin-2-one.

Sources & evidence

ORD record
ord-77968a970383497fb5f05f85b794ea24
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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