Carbon Dioxide → (r)-2'-Propoxy-7'-(5-pyrimidinyl)spiro[1,3-oxazole-4,9'-xanthen]-2-amine

HRID 335685Notes

Reaction equation

HRID 335685 reaction equation
[CH2:1]([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)[CH2:2][CH3:3].C(=O)=O>CO>[CH2:1]([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)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 280Carbon DioxideHCID 452559172'-Propoxy-7'-(5-pyrimidinyl)spiro[1,3-oxazole-4,9'-xanthen]-2-amine

Product 1

HCID 45256105(r)-2'-Propoxy-7'-(5-pyrimidinyl)spiro[1,3-oxazole-4,9'-xanthen]-2-amineYield 32.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2′-Propoxy-7′-(5-pyrimidinyl)spiro[1,3-oxazole-4,9′-xanthen]-2-amine (40 mg) was subjected to chromatography using 15:85:0.2 MeOH:CO2:DEA at 80 ml/min on a 20×250 mm, 5 μm ChiralPak AS-H column and 100-bar system pressure. The first peak (RT=3.5 min) provided (R)-2′-propoxy-7′-(5-pyrimidinyl)spiro[1,3-oxazole-4,9′-xanthen]-2-amine (13.0 mg, >99% ee), and the second peak (RT=4.3 min) provided (S)-2′-propoxy-7′-(5-pyrimidinyl)spiro[1,3-oxazole-4,9′-xanthen]-2-amine (12.8 mg, >99% ee).

Sources & evidence

ORD record
ord-1b0e5f72a7d44099b92d88c7d3c1bce3
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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