Sodium Hydroxide → HCID 58136305, compound

HRID 877272Notes

Reaction equation

HRID 877272 reaction equation
[CH3:1][C:2]1[C:7]([NH:8][C:9](=[O:35])[CH:10]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][N:22]3[C:27](=[O:28])[CH2:26][O:25][C:24]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[N:23]3)=[CH:17][CH:16]=2)[CH:11]([CH3:14])[CH2:12][CH3:13])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:36][CH2:37][C:38]([O:40]CC)=[O:39].[OH-].[Na+]>C1COCC1>[CH3:1][C:2]1[C:7]([NH:8][C:9](=[O:35])[CH:10]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][N:22]3[C:27](=[O:28])[CH2:26][O:25][C:24]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)=[N:23]3)=[CH:17][CH:16]=2)[CH:11]([CH3:14])[CH2:12][CH3:13])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:36][CH2:37][C:38]([OH:40])=[O:39]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58136719HCID 58136719, compound

Product 1

HCID 58136305HCID 58136305, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 175 mg (0.31 mmol) of ethyl 3-{2-methyl-3-[(3-methyl-2-{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}pentanoyl)amino]phenyl}propanoate (Example 151A) in 5.5 ml of THF and 1.2 ml (1.2 mmol) of 1 N aqueous sodium hydroxide solution was stirred at 60° C. overnight. 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 165 mg (0.30 mmol, 99% 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 165 mg (0.30 mmol, 99% of theory) of the title compound as a mixture of isomers

Sources & evidence

ORD record
ord-7519b62de1e44774b87e195a0cf7274c
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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