Water → HCID 71186338, compound

HRID 712908Notes

Reaction equation

HRID 712908 reaction equation
[F:1][C:2]1([F:35])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[CH:4]([C:19]([NH:21][C:22]2([C:25]3[CH:34]=[CH:33][C:28]([C:29]([O:31]C)=[O:30])=[CH:27][CH:26]=3)[CH2:24][CH2:23]2)=[O:20])[CH2:3]1.O>O1CCOCC1>[F:35][C:2]1([F:1])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[CH:4]([C:19]([NH:21][C:22]2([C:25]3[CH:26]=[CH:27][C:28]([C:29]([OH:31])=[O:30])=[CH:33][CH:34]=3)[CH2:24][CH2:23]2)=[O:20])[CH2:3]1

Participants

4

Reactant 2

HCID 962WaterHCID 71186414HCID 71186414, compound

Product 1

HCID 71186338HCID 71186338, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 4-(1-(4,4-difluoro-1-(4-(trifluoromethyl)benzyl)piperidine-2-carboxamido)cyclopropyl)benzoate (enantiomer 1) (D137a) (140 mg, 0.28 mmol) in dioxane (3 ml) and water (3 ml) LiOH H2O (47 mg, 1.12 mmol) was added and the mixture was left stirring at RT for 16 hrs. Dioxane was evaporated off then acetic acid was added to the aqueous layer until the solution reached the value of p≈4. The solid was filtered off and dried under vacuum to afford the title compound (E18) (90 mg)

Workup

  1. waitthe mixture was left
  2. customDioxane was evaporated off
  3. additionacetic acid was added to the aqueous layer until the solution
  4. filtrationThe solid was filtered off
  5. customdried under vacuum

Sources & evidence

ORD record
ord-65430117b53d493fa6526f604c5988fb
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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