Sodium Hydroxide → HCID 22860742, compound

HRID 2295121Notes

Reaction equation

HRID 2295121 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][O:7][C@H:8]1[O:13][CH2:12][CH2:11][N:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21]C)=[O:20])[C@@H:9]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH-].[Na+]>CO>[F:37][C:2]([F:1])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:31]=1)[CH2:6][O:7][C@H:8]1[O:13][CH2:12][CH2:11][N:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C@@H:9]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22860743HCID 22860743, compound

Product 1

HCID 22860742HCID 22860742, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.15 g (0.28 mmol) of 2-(S)-(3,5-Bis(trifluoromethyl)benzyloxy)-4-(methoxycarbonylpentyl)-3-(R)-phenylmorpholine (from Example 64) in 3 mL of MeOH was saponified by treating with 0.5 mL of 5N NaOH for 40 min at 65° C. The solution was cooled, concentrated and the residue was diluted with water. The aqueous solution was adjusted to pH 6 by adding 2N HCl and it was extracted with EtOAc. The organic layer was washed with brine, dried and concentrated. The residue upon chromatography on a flash column with 50% EtOAc/hexane furnished 0.13 g (89%) of the product.

Workup

  1. temperatureThe solution was cooled
  2. concentrationconcentrated
  3. additionthe residue was diluted with water
  4. additionby adding 2N HCl and it
  5. extractionwas extracted with EtOAc
  6. washThe organic layer was washed with brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-54668b9a7e344d3daa48f04882a89666
Source dataset
uspto-grants-1997_11
Patent number
US05691336

Reaction notes

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