Isopropanol → HCID 86730239, compound

HRID 1850200Notes

Reaction equation

HRID 1850200 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([CH:11]([NH:13][C:14]3[N:19]=[C:18]([N:20]4[C@@H:24]([CH:25]([CH3:27])[CH3:26])[CH2:23][O:22][C:21]4=[O:28])[CH:17]=[CH:16][N:15]=3)[CH3:12])[CH:9]=[CH:10][C:2]1=2.CC(O)C>C(=O)=O>[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C@H:11]([NH:13][C:14]3[N:19]=[C:18]([N:20]4[C@@H:24]([CH:25]([CH3:27])[CH3:26])[CH2:23][O:22][C:21]4=[O:28])[CH:17]=[CH:16][N:15]=3)[CH3:12])[CH:9]=[CH:10][C:2]1=2.[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C@@H:11]([NH:13][C:14]3[N:19]=[C:18]([N:20]4[C@@H:24]([CH:25]([CH3:27])[CH3:26])[CH2:23][O:22][C:21]4=[O:28])[CH:17]=[CH:16][N:15]=3)[CH3:12])[CH:9]=[CH:10][C:2]1=2

Participants

5

Reactant 2

HCID 3776IsopropanolHCID 86730241HCID 86730241, compound

Product 2

HCID 86730239HCID 86730239, compoundHCID 86730240HCID 86730240, compound

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

(4S)-3-(2-(1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one (example 130, 52 mg) was resolved on a column (IA 4.6×100 mm) using 40% iPrOH in CO2 to give (S)-3-(2-((R)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one and (S)-3-(2-((S)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one.

Sources & evidence

ORD record
ord-6d11125049824f23bde617303456ee75
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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