Hydrochloric Acid → HCID 44517482, compound

HRID 877260Notes

Reaction equation

HRID 877260 reaction equation
O.[OH-].[Li+].[CH3:4][C:5]1([C:41]([O:43]C)=[O:42])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:14][C:15](=[O:40])[CH:16]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][N:27]3[C:32](=[O:33])[CH2:31][O:30][C:29]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[N:28]3)=[CH:22][CH:21]=2)[CH:17]([CH3:19])[CH3:18])[CH2:6]1.Cl>C1COCC1.O>[CH3:4][C:5]1([C:41]([OH:43])=[O:42])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:14][C:15](=[O:40])[CH:16]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][N:27]3[C:32](=[O:33])[CH2:31][O:30][C:29]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[N:28]3)=[CH:22][CH:21]=2)[CH:17]([CH3:19])[CH3:18])[CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 58136602HCID 58136602, compound

Product 1

HCID 44517482HCID 44517482, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

9.1 mg (0.22 mmol) of lithium hydroxide monohydrate were added to a solution of 60 mg (0.11 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}butanoyl)amino]-2,3-dihydro-1H-indene-2-carboxylate (Example 136A) in 2 ml of THF and 2 ml of water, and the mixture was stirred at 60° C. for 8 h. The reaction mixture was then adjusted to pH 4 with 1 M hydrochloric acid and concentrated to dryness under reduced pressure. The crude product obtained was purified by flash chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1→4:1→1:1 or dichloromethane/methanol 10:1). This gave 43 mg (0.08 mmol, 74% of theory) of the title compound.

Workup

  1. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f3f9ad3d97d549b09c53066c43182070
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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