Hydrochloric Acid → HCID 58136411, compound

HRID 877268Notes

Reaction equation

HRID 877268 reaction equation
O.[OH-].[Li+].[CH3:4][CH:5]([CH3:42])[CH:6]([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][N:29]2[C:34](=[O:35])[CH2:33][O:32][C:31]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[N:30]2)=[CH:24][CH:23]=1)[C:7]([NH:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH:12]([CH2:16][CH2:17][C:18]([O:20]C)=[O:19])[CH2:11]1)=[O:8].Cl>C1COCC1.O>[CH3:4][CH:5]([CH3:42])[CH:6]([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][N:29]2[C:34](=[O:35])[CH2:33][O:32][C:31]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[N:30]2)=[CH:24][CH:23]=1)[C:7]([NH:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH:12]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH2:11]1)=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 58136321HCID 58136321, compound

Product 1

HCID 58136411HCID 58136411, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

94 mg (2.25 mmol) of lithium hydroxide monohydrate were added to a solution of 600 mg (1.12 mmol) of methyl 3-{3-[(3-methyl-2-{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}butanoyl)amino]cyclohexyl}propanoate (Example 142A) in 15 ml of THF and 15 ml of water, and the mixture was stirred at room temperature overnight. The reaction mixture was then adjusted to pH 2 with 1 M hydrochloric acid and extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure. This gave 573 mg (1.10 mmol, 98% of theory) of the title compound as a mixture of isomers.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure
  5. additionThis gave 573 mg (1.10 mmol, 98% of theory) of the title compound as a mixture of isomers

Sources & evidence

ORD record
ord-3f6ed9cb5fdc42858f979918dd541adc
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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