Hydrochloric Acid → HCID 58136410, compound

HRID 877267Notes

Reaction equation

HRID 877267 reaction equation
O.[OH-].[Li+].[F:4][C:5]([F:46])([F:45])[CH2:6][CH2:7][CH:8]([C:25]1[CH:30]=[CH:29][C:28]([CH2:31][N:32]2[C:37](=[O:38])[CH2:36][O:35][C:34]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[N:33]2)=[CH:27][CH:26]=1)[C:9]([NH:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH2:14][CH:15]([C:21]([O:23]C)=[O:22])[CH2:16]2)=[O:10].Cl>C1COCC1.O>[F:46][C:5]([F:4])([F:45])[CH2:6][CH2:7][CH:8]([C:25]1[CH:30]=[CH:29][C:28]([CH2:31][N:32]2[C:37](=[O:38])[CH2:36][O:35][C:34]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[N:33]2)=[CH:27][CH:26]=1)[C:9]([NH:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH2:14][CH:15]([C:21]([OH:23])=[O:22])[CH2:16]2)=[O:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 58136331HCID 58136331, compound

Product 1

HCID 58136410HCID 58136410, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

32 mg (0.76 mmol) of lithium hydroxide monohydrate were added to a solution of 112 mg (0.19 mmol) of methyl 4-[(5,5,5-trifluoro-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 143A) in 2 ml of THF and 1 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. The residue obtained was purified by preparative HPLC. This gave 74 mg (0.13 mmol, 68% 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. customThe residue obtained
  6. customwas purified by preparative HPLC
  7. additionThis gave 74 mg (0.13 mmol, 68% of theory) of the title compound as a mixture of diastereomers

Sources & evidence

ORD record
ord-9058c71ea28748de9914261e574022f1
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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