Sodium Hydroxide → HCID 22860742, compound

HRID 1004099Notes

Reaction equation

HRID 1004099 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 5 N 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 2 N 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 2 N 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-c321b2d1d36445c48eb99d195c6150a2
Source dataset
uspto-grants-2000_04
Patent number
US06048859

Reaction notes

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