Sodium Hydroxide → HCID 44513410, compound

HRID 877271Notes

Reaction equation

HRID 877271 reaction equation
[CH3:1][CH:2]([CH2:39][CH3:40])[CH:3]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[C:31](=[O:32])[CH2:30][O:29][C:28]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[N:27]2)=[CH:21][CH:20]=1)[C:4]([NH:6][CH2:7][CH:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16]CC)=[O:15])[CH2:10][CH2:9]1)=[O:5].[OH-].[Na+]>C1COCC1>[CH3:1][CH:2]([CH2:39][CH3:40])[CH:3]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[C:31](=[O:32])[CH2:30][O:29][C:28]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[N:27]2)=[CH:21][CH:20]=1)[C:4]([NH:6][CH2:7][CH:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58136376HCID 58136376, compound

Product 1

HCID 44513410HCID 44513410, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 492 mg (0.90 mmol) of ethyl 4-{[(3-methyl-2-{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}pentanoyl)amino]methyl}cyclohexanecarboxylate (Example 150A) in 8 ml of THF and 4.6 ml (4.6 mmol) of 1 N aqueous sodium hydroxide solution was stirred at 60° C. for four days. After the reaction had gone to completion, the THF was removed under reduced pressure and the reaction solution was diluted with water and then adjusted to pH 2 with 1 M hydrochloric acid. The precipitated solid was filtered off, washed with water and dried under reduced pressure at 45° C. overnight. This gave 343 mg (0.66 mmol, 73% of theory) of the title compound as a mixture of isomers.

Workup

  1. customthe THF was removed under reduced pressure
  2. additionthe reaction solution was diluted with water
  3. filtrationThe precipitated solid was filtered off
  4. washwashed with water
  5. customdried under reduced pressure at 45° C. overnight
  6. additionThis gave 343 mg (0.66 mmol, 73% of theory) of the title compound as a mixture of isomers

Sources & evidence

ORD record
ord-af7b1bce059e4a4497d8cb6746f1b47e
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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