Water → HCID 57378888, compound

HRID 72554Notes

Reaction equation

HRID 72554 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:23]2[CH2:27][CH2:26][CH:25]([O:28][C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=3)[CH2:24]2)=[C:6]([CH:22]=1)[C:7]([NH:9][C@H:10]([C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=1)[CH3:11])=[O:8].O>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:23]2[CH2:27][CH2:26][CH:25]([O:28][C:29]3[CH:30]=[CH:31][C:32]([C:35]([F:36])([F:38])[F:37])=[CH:33][CH:34]=3)[CH2:24]2)=[C:6]([CH:22]=1)[C:7]([NH:9][C@H:10]([C:12]1[CH:21]=[CH:20][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1)[CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 962WaterHCID 67958125methyl 4-((1S)-1-(5-chloro-2-(3-(4-(trifluoromethyl)phenoxy)pyrrolidin-1-yl)nicotinamido)ethyl)benzoate

Product 1

HCID 57378888HCID 57378888, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 4-((1S)-1-(5-chloro-2-(3-(4-(trifluoromethyl)phenoxy)pyrrolidin-1-yl)nicotinamido)ethyl)benzoate (D191) (50 mg, 0.091 mmol) in 1,4-dioxane (3 ml) and water (1 ml) lithium hydroxide monohydrate (5.8 mg, 0.14 mmol) was added and the resulting mixture was stirred at room temperature for 2 days. Solvents were evaporated in vacuo. The residue was diluted with water (5 ml) and 1M HCl (15 ml) and extracted with ethylacetate (3×20 ml). Collected organics, after solvent evaporation, afforded the title compound (E57) (40 mg).

Workup

  1. customSolvents were evaporated in vacuo
  2. additionThe residue was diluted with water (5 ml) and 1M HCl (15 ml)
  3. extractionextracted with ethylacetate (3×20 ml)
  4. customCollected organics, after solvent evaporation

Sources & evidence

ORD record
ord-0926bb11c5c24e0ba2f8bae06d528937
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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