HCID 67608562, compound → HCID 67608348, compound

HRID 63945Notes

Reaction equation

HRID 63945 reaction equation
[C:1]([O:5][CH:6]([C:10]1[C:11]([C:24]2[CH:25]=[N:26][CH:27]=[N:28][CH:29]=2)=[C:12]2[C:19]3[CH2:20][CH2:21][CH2:22][CH2:23][C:18]=3[S:17][C:13]2=[N:14][C:15]=1[CH3:16])[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]>CO.ClCCl>[C:1]([O:5][C@@H:6]([C:10]1[C:11]([C:24]2[CH:25]=[N:26][CH:27]=[N:28][CH:29]=2)=[C:12]2[C:19]3[CH2:20][CH2:21][CH2:22][CH2:23][C:18]=3[S:17][C:13]2=[N:14][C:15]=1[CH3:16])[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67608562HCID 67608562, compound

Product 1

HCID 67608348HCID 67608348, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A sample of the product from Example 1 may be dissolved in a mixture of methanol and dichloromethane (1:1) loaded onto a Chiralpak IC column (250×20 mm internal diameter) and eluted with methanol/CO2 (60:40) at ambient temperature and a flow rate of 60 g/min. Fractions containing a single enantiomer may be combined and evaporated under reduced pressure to give the product enantiomer. Chiral purity may be assessed by chiral hplc using a Chiralpak IC column eluting with hexane/isopropanol.

Workup

  1. washeluted with methanol/CO2 (60:40) at ambient temperature
  2. additionFractions containing a single enantiomer
  3. customevaporated under reduced pressure
  4. customto give the product enantiomer
  5. washeluting with hexane/isopropanol

Sources & evidence

ORD record
ord-c85e34cd450a4e328c66ef3853557124
Source dataset
uspto-grants-2016_09
Patent number
US09447116B2

Reaction notes

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