HCID 86754235, compound → HCID 86754236, compound

HRID 582233Notes

Reaction equation

HRID 582233 reaction equation
[C:1]1([CH2:7][O:8][C:9]([N:11]2[CH2:20][CH2:19][N:18]3[CH:13]([CH2:14][O:15][C:16]4[CH:24]=[C:23]([N:25]5[CH2:29][C@H:28]([CH2:30][OH:31])[O:27][C:26]5=[O:32])[CH:22]=[CH:21][C:17]=43)[CH2:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CCCCCC.CCO>[C:1]1([CH2:7][O:8][C:9]([N:11]2[CH2:20][CH2:19][N:18]3[C@H:13]([CH2:14][O:15][C:16]4[CH:24]=[C:23]([N:25]5[CH2:29][C@H:28]([CH2:30][OH:31])[O:27][C:26]5=[O:32])[CH:22]=[CH:21][C:17]=43)[CH2:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 86754235HCID 86754235, compound

Product 1

HCID 86754236HCID 86754236, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 50 mg/mL of a mixture of diastereomers 1, 2, 4a, 5-Tetrahydro-8-[5-(R)-(hydroxymethyl)-2-oxo-3-oxazolidinyl]-pyrazino[2, 1-c][1, 4]benzoxazine-3(4 H)-carboxylic acid phenylmethyl ester (EXAMPLE 1, Step 8) is made in the mobile phase that consisted of 35% EtOH in hexane (V/V). The solution (200 mg) is injected into a 5.1×50 cm Chiralcel OD column at 30° C. The column is eluted at 45 ml/min and monitored at 305 nm. The two diastereomers are collected using a peak recognition program and fractions are pooled appropriately. Each diastereomer is obtained at >98% diastereomer excess. Diastereomeric excess is determined on a 0.46×25 cm Chiralcel OD-H column at ambient column temperature, using the mobile phase consisted of 0.1% TEA in EtOH and the monitor set at 218 nm detection. The retention times are 58.9 and 65.6 minutes. (α=1.14; 0.2 mL/min).

Workup

  1. customis injected into a 5.1×50 cm Chiralcel OD column at 30° C
  2. washThe column is eluted at 45 ml/min
  3. customThe two diastereomers are collected
  4. customEach diastereomer is obtained at >98% diastereomer excess
  5. custom58.9 and 65.6 minutes

Sources & evidence

ORD record
ord-a960fd348d9e4f148fbda54219be0ed0
Source dataset
uspto-grants-1999_07
Patent number
US05922707

Reaction notes

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