Methanol → HCID 15907893, compound

HRID 1019416Notes

Reaction equation

HRID 1019416 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[NH:5][C:6]([CH2:8][C:9]1[CH:20]=[CH:19][C:12]([O:13][CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:11][CH:10]=1)=[O:7].[CH3:25]O>C(O)C>[CH3:24][C:22]1[CH:21]=[C:4]([CH:3]=[C:2]([CH3:1])[CH:23]=1)[NH:5][C:6]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH:14]([CH2:18][CH3:25])[C:15]([OH:17])=[O:16])=[CH:19][CH:20]=1)=[O:7]

Participants

4

Reactant 2

HCID 887MethanolHCID 15907892HCID 15907892, compound

Product 1

HCID 15907893HCID 15907893, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mother liquor from the recrystallization of (−) 20-cinchonidine salt was concentrated under reduced pressure. The enriched (+) 20 isomer was obtained from the mother liquor by neutralizing the salt to obtain the free acid, as described previously for compound 18. The optical rotation showed that the isomer was approximately 80% enantiomeric excess, optical rotation was measured at 21° C.: [α]D +18:2° (c=1.2, methanol). A stock solution (1 mg/mL) of the racemic mixture (20) was prepared in ethanol/mobile phase (1:1). The injected sample volume was 250 μL. The compound was eluted with a mobile phase of heptane/ethanol. with 1% TFA (88:12) at a flow rate of 2.5 mL/min. Under these conditions, the (−) isomer eluted at 15.8 min and the (+) isomer eluted at 18.2 min retention times. The collected fractions were concentrated under reduced pressure at room temperature. (+) 20 was collected as a white solid, 0.14 g. mp 146-148° C. The optical rotation was measured at 21° C.: [α]D +25.3° (c=0.5, methanol).

Workup

  1. customThe mother liquor from the recrystallization of (−) 20-cinchonidine salt
  2. concentrationwas concentrated under reduced pressure
  3. customwas obtained from the mother liquor
  4. customto obtain the free acid
  5. customwas measured at 21° C.
  6. washThe compound was eluted with a mobile phase of heptane/ethanol
  7. washUnder these conditions, the (−) isomer eluted at 15.8 min
  8. washthe (+) isomer eluted at 18.2 min retention times
  9. concentrationThe collected fractions were concentrated under reduced pressure at room temperature
  10. custom(+) 20 was collected as a white solid, 0.14 g
  11. customwas measured at 21° C.

Sources & evidence

ORD record
ord-63d6800c8262438caebc08122080c469
Source dataset
uspto-grants-2002_11
Patent number
US06486342B1

Reaction notes

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