Methanol → HCID 86730254, compound

HRID 1850206Notes

Reaction equation

HRID 1850206 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:13]([CH3:15])([CH3:14])[O:12][C:11](=[O:16])[N:10]2[C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C@H:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:25])[N:18]=2)=[CH:5][CH:4]=1.CO.N(CC)CC>C(=O)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[C:13]([CH3:14])([CH3:15])[O:12][C:11](=[O:16])[N:10]2[C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C@H:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:25])[N:18]=2)=[CH:7][CH:8]=1.[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@@H:9]2[C:13]([CH3:14])([CH3:15])[O:12][C:11](=[O:16])[N:10]2[C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C@H:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:25])[N:18]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 8021DiethylamineHCID 86730256HCID 86730256, compound

Product 2

HCID 86730254HCID 86730254, compoundHCID 86730255HCID 86730255, compound

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

4-(4-methoxyphenyl)-5,5-dimethyl-3-(2-((S)-1-phenylethylamino)pyrimidin-4-yl)oxazolidin-2-one (example 54, 62 mg) was resolved in on a column (AD-H 4.6×100 mm) with 30% MeOH modified with 0.2% Et2NH in CO2 to give (S)-4-(4-methoxyphenyl)-5,5-dimethyl-3-(2-((S)-1-phenylethylamino)pyrimidin-4-yl)oxazolidin-2-one and (R)-4-(4-methoxyphenyl)-5,5-dimethyl-3-(2-((S)-1-phenylethylamino)pyrimidin-4-yl)oxazolidin-2-one.

Sources & evidence

ORD record
ord-58390fe639214c1ab8e78c15a0d99361
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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