Sodium Hydroxide → N-[4-(2,2-difluoroethyl)oxy-3-hydroxycarbonyl-phenyl]-2-chloro-5-(tert-butylcarbonylamino)methyl-benzamide

HRID 1846087Notes

Reaction equation

HRID 1846087 reaction equation
[F:1][CH:2]([F:34])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:28])[C:13]2[CH:18]=[C:17]([CH2:19][NH:20][C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22])[CH:16]=[CH:15][C:14]=2[Cl:27])=[CH:7][C:6]=1[C:29]([O:31]CC)=[O:30].[OH-].[Na+]>CCO>[F:34][CH:2]([F:1])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:28])[C:13]2[CH:18]=[C:17]([CH2:19][NH:20][C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22])[CH:16]=[CH:15][C:14]=2[Cl:27])=[CH:7][C:6]=1[C:29]([OH:31])=[O:30]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 87275046N-[4-(2,2-Difluoroethyl)oxy-3-ethoxycarbonyl-phenyl]-2-chloro-5-(tert-butylcarbonylamino)methyl-benzamide

Product 1

HCID 86658668N-[4-(2,2-difluoroethyl)oxy-3-hydroxycarbonyl-phenyl]-2-chloro-5-(tert-butylcarbonylamino)methyl-benzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-[4-(2,2-difluoroethyl)oxy-3-ethoxycarbonyl-phenyl]-2-chloro-5-(tert-butylcarbonylamino)methyl-benzamide (0.470 mg, 0.946 mmol) and 1.4 mL 2M NaOH in 5.0 mL EtOH was stirred at rt for 3 h and concentrated i.vac. Water was added and it was acidified with 2 M HCl. The resulting precipitate was filtered, washed with water and dried. Yield: (86%). MS [M+H]+=469 (Cl isotope pattern); TLC: Rf=0.25 (silica gel, DCM:EtOH 9:1).

Workup

  1. concentrationconcentrated i.vac
  2. additionWater was added
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-8a22831937c947078c14f585e14c31c0
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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