Sodium Hydroxide → HCID 44513409, compound

HRID 877270Notes

Reaction equation

HRID 877270 reaction equation
[CH3:1][CH:2]([CH2:40][CH3:41])[CH:3]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][N:27]2[C:32](=[O:33])[CH2:31][O:30][C:29]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[N:28]2)=[CH:22][CH:21]=1)[C:4]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][CH:10]([C:16]([O:18]C)=[O:17])[CH2:11]2)=[O:5].[OH-].[Na+]>C1COCC1>[CH3:1][CH:2]([CH2:40][CH3:41])[CH:3]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][N:27]2[C:32](=[O:33])[CH2:31][O:30][C:29]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[N:28]2)=[CH:22][CH:21]=1)[C:4]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][CH:10]([C:16]([OH:18])=[O:17])[CH2:11]2)=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58136310HCID 58136310, compound

Product 1

HCID 44513409HCID 44513409, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 180 mg (0.31 mmol) of methyl 4-[(3-methyl-2-{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}pentanoyl)amino]-2,3-dihydro-1H-indene-2-carboxylate (Example 147A) in 3.6 ml of THF and 1.3 ml (1.3 mmol) of 1 N aqueous sodium hydroxide solution was stirred at room temperature 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 159 mg (0.29 mmol, 91% 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 159 mg (0.29 mmol, 91% of theory) of the title compound as a mixture of isomers

Sources & evidence

ORD record
ord-506cd3df9af64af2991b691e4d02a149
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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