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

HRID 1631702Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1631702
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9e3e23737d944ccbbd226c02d448833d
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791107B2

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