(S)-morpholine-3-carboxylic acid → (R)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

HRID 2169540Notes

Reaction equation

HRID 2169540 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[NH:8][CH2:7][CH:6]3[CH2:12][O:13][CH2:14][CH2:15][N:5]3[C:4]=2[N:3]=1.N1CCOC[C@H]1C(O)=O>CO>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[NH:8][CH2:7][C@@H:6]3[CH2:12][O:13][CH2:14][CH2:15][N:5]3[C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 1501894(S)-morpholine-3-carboxylic acidHCID 86670087HCID 86670087, compound

Product 1

HCID 86670088(R)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An enantiomeric mixture of 2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x2, 8 g) was dissolved in MeOH (400 mL) and was separated by supercritical fluid chromatography (SFC) (Chiralcel® AS-H (5 μm, 20×150 mm), 20% MeOH in liquid CO2 at 55 mL/min, 3 mL/injection). The peak eluting at ˜5 minutes was collected. The stereo-configuration was assigned based on a comparison of retention times of an enantiomerically-enriched sample synthesized in a manner similar to PREPARATION x1 and PREPARATION x2 using optically pure (S)-morpholine-3-carboxylic acid.

Workup

  1. customwas separated by supercritical fluid chromatography (SFC) (Chiralcel® AS-H (5 μm, 20×150 mm), 20% MeOH in liquid CO2 at 55 mL/min, 3 mL/injection)
  2. washThe peak eluting at ˜5 minutes
  3. customwas collected
  4. customsynthesized in a manner similar to PREPARATION x1 and PREPARATION x2

Sources & evidence

ORD record
ord-b885ef779c5a4fc98e7cd39bd53eb96e
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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