Lithium hydroxide, monohydrate → HCID 44513411, compound

HRID 877273Notes

Reaction equation

HRID 877273 reaction equation
O.[OH-].[Li+].[CH3:4][C:5]1([C:42]([O:44]C)=[O:43])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:14][C:15](=[O:41])[CH:16]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][N:28]3[C:33](=[O:34])[CH2:32][O:31][C:30]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[N:29]3)=[CH:23][CH:22]=2)[CH:17]([CH3:20])[CH2:18][CH3:19])[CH2:6]1>C1COCC1.O>[CH3:4][C:5]1([C:42]([OH:44])=[O:43])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:14][C:15](=[O:41])[CH:16]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][N:28]3[C:33](=[O:34])[CH2:32][O:31][C:30]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)=[N:29]3)=[CH:23][CH:22]=2)[CH:17]([CH3:20])[CH2:18][CH3:19])[CH2:6]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58136635HCID 58136635, compound

Product 1

HCID 44513411HCID 44513411, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

100 mg (2.39 mmol) of lithium hydroxide monohydrate were added to a solution of 339 mg (0.60 mmol) of methyl 2-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 160A) in 12 ml of THF and 6 ml of water, and the mixture 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 305 mg (0.55 mmol, 92% 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 305 mg (0.55 mmol, 92% of theory) of the title compound as a mixture of isomers

Sources & evidence

ORD record
ord-f7db1a45b9bd45de8af5bd656a5ee0e7
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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