Hydrochloric Acid → HCID 58136373, compound

HRID 877265Notes

Reaction equation

HRID 877265 reaction equation
O.[OH-].[Li+].[CH:4]1([CH:9]([C:27]2[CH:32]=[CH:31][C:30]([CH2:33][N:34]3[C:39](=[O:40])[CH2:38][O:37][C:36]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)=[N:35]3)=[CH:29][CH:28]=2)[C:10]([NH:12][C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[CH2:15][C:16]([CH3:26])([C:22]([O:24]C)=[O:23])[CH2:17]3)=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5]1.Cl>C1COCC1.O>[CH:4]1([CH:9]([C:27]2[CH:28]=[CH:29][C:30]([CH2:33][N:34]3[C:39](=[O:40])[CH2:38][O:37][C:36]([C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)=[N:35]3)=[CH:31][CH:32]=2)[C:10]([NH:12][C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[CH2:15][C:16]([CH3:26])([C:22]([OH:24])=[O:23])[CH2:17]3)=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 58136386HCID 58136386, compound

Product 1

HCID 58136373HCID 58136373, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

11 mg (0.26 mmol) of lithium hydroxide monohydrate were added to a solution of 74 mg (0.13 mmol) of methyl 4-[(cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetyl)amino]-2-methyl-2,3-dihydro-1H-indene-2-carboxylate (Example 131A) in 2 ml of THF and 1 ml of water, and the mixture was stirred at room temperature for 12 h. 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 64 mg (0.11 mmol, 88% of theory) of the title compound as a mixture of diastereomers.

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 64 mg (0.11 mmol, 88% of theory) of the title compound as a mixture of diastereomers

Sources & evidence

ORD record
ord-4cf9c9983731434c99a5bf0f21d63a39
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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