Carbon Dioxide → (4s)-2'-(3,3-Dimethylbut-1-ynyl)-7'-(pyrimidin-5-yl)-5h-spiro[oxazole-4,9'-xanthen]-2-amine

HRID 1970256Notes

Reaction equation

HRID 1970256 reaction equation
[CH3:1][C:2]([CH3:31])([CH3:30])[C:3]#[C:4][C:5]1[CH:18]=[CH:17][C:16]2[O:15][C:14]3[C:9](=[CH:10][C:11]([C:19]4[CH:20]=[N:21][CH:22]=[N:23][CH:24]=4)=[CH:12][CH:13]=3)[C:8]3([CH2:28][O:27][C:26]([NH2:29])=[N:25]3)[C:7]=2[CH:6]=1.C(=O)=O>CO>[CH3:1][C:2]([CH3:31])([CH3:30])[C:3]#[C:4][C:5]1[CH:18]=[CH:17][C:16]2[O:15][C:14]3[C:9](=[CH:10][C:11]([C:19]4[CH:20]=[N:21][CH:22]=[N:23][CH:24]=4)=[CH:12][CH:13]=3)[C@:8]3([CH2:28][O:27][C:26]([NH2:29])=[N:25]3)[C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 280Carbon DioxideHCID 58466325(Rac)-2'-(3,3-dimethylbut-1-ynyl)-7'-(pyrimidin-5-yl)-5h-spiro[oxazole-4,9'-xanthen]-2-amine

Product 1

HCID 67246953(4s)-2'-(3,3-Dimethylbut-1-ynyl)-7'-(pyrimidin-5-yl)-5h-spiro[oxazole-4,9'-xanthen]-2-amineYield 41.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Racemic 2′-(3,3-dimethylbut-1-ynyl)-7′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (490 mg) was subjected to chromatography using 20:80:0.1 MeOH:CO2:DEA at 65 ml/min on a 20×150 mm ChiralPak AD-H column and 100-bar system pressure. The first peak (RT=3.51 min) provided (4S)-2′-(3,3-dimethylbut-1-ynyl)-7′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (204 mg, 99% ee), and the second peak (RT=5.44 min) provided (4R)-2′-(3,3-dimethylbut-1-ynyl)-7′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (>99% ee).

Sources & evidence

ORD record
ord-b5b506a601e44e6f820b16b7b2220254
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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