Carbon Dioxide → HCID 67248077, compound

HRID 1970242Notes

Reaction equation

HRID 1970242 reaction equation
[CH3:1][C:2]([CH3:31])([CH3:30])[CH2:3][O: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])[CH2:3][O: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 46178256HCID 46178256, compound

Product 1

HCID 67248077HCID 67248077, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2′-(2,2-Dimethylpropoxy)-7′-(5-pyrimidinyl)spiro[1,3-oxazole-4,9′-xanthen]-2-amine (139 mg) was subjected to chromatography using 40:60:0.2 MeOH:CO2:DEA at 70 ml/min on a 20×250 mm, 5 μm ChiralPak AD-H column and 100-bar system pressure. The first peak (RT=2.0 min) provided (R)-2′-(2,2-dimethylpropoxy)-7′-(5-pyrimidinyl)spiro[1,3-oxazole-4,9′-xanthen]-2-amine (50.9 mg, >99% ee), and the second peak (RT=3.9 min) provided (S)-2′-(2,2-dimethylpropoxy)-7′-(5-pyrimidinyl)spiro[1,3-oxazole-4,9′-xanthen]-2-amine (52.7 mg, >99% ee).

Sources & evidence

ORD record
ord-97de6554dd1140769dfb7c3838dea0d8
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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