Lithium hydroxide, monohydrate → (1-{3-[(Cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}-acetyl)amino]propyl}cyclopropyl)acetic Acid

HRID 238191Notes

Reaction equation

HRID 238191 reaction equation
O.[OH-].[Li+].[CH:4]1([CH:9]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][N:31]3[C:36](=[O:37])[CH2:35][O:34][C:33]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[N:32]3)=[CH:26][CH:25]=2)[C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]2([CH2:19][C:20]([O:22]C)=[O:21])[CH2:18][CH2:17]2)=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5]1>C1COCC1.O>[CH:4]1([CH:9]([C:24]2[CH:25]=[CH:26][C:27]([CH2:30][N:31]3[C:36](=[O:37])[CH2:35][O:34][C:33]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[N:32]3)=[CH:28][CH:29]=2)[C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]2([CH2:19][C:20]([OH:22])=[O:21])[CH2:18][CH2:17]2)=[O:11])[CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58074543Methyl (1-{3-[(cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]-phenyl}acetyl)amino]propyl}cyclopropyl)acetate

Product 1

HCID 46909293(1-{3-[(Cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}-acetyl)amino]propyl}cyclopropyl)acetic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

71 mg (1.69 mmol) of lithium hydroxide monohydrate were added to a solution of 230 mg (0.42 mmol) of methyl (1-{3-[(cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetyl)amino]propyl}cyclopropyl)acetate in 2.8 ml of THF and 1.4 ml of water, and the mixture was stirred at RT 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 217 mg (0.41 mmol, 97% of theory) of the title compound as a white solid.

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

Sources & evidence

ORD record
ord-fee9f221270248418842b40b3f644dd4
Source dataset
uspto-grants-2014_02
Patent number
US08642592B2

Reaction notes

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