Lithium Hydroxide → {Tert-butyl-[3-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-benzoyl]-amino}-acetic acid

HRID 1665257Notes

Reaction equation

HRID 1665257 reaction equation
C([O:3][C:4](=[O:37])[CH2:5][N:6]([C:11](=[O:36])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[C:30]([F:32])[C:29]([F:33])=[CH:28][C:27]=3[O:34][CH3:35])=[CH:22][CH:21]=2)[CH:13]=1)[C:7]([CH3:10])([CH3:9])[CH3:8])C.[Li+].[OH-]>C1COCC1.O>[C:7]([N:6]([CH2:5][C:4]([OH:37])=[O:3])[C:11](=[O:36])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[C:30]([F:32])[C:29]([F:33])=[CH:28][C:27]=3[O:34][CH3:35])=[CH:22][CH:21]=2)[CH:13]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67152350{[3-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-benzoyl]-tert-butyl-amino}-acetic acid ethyl ester

Product 1

HCID 52933305{Tert-butyl-[3-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-benzoyl]-amino}-acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of {[3-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-benzoyl]-tert-butyl-amino}-acetic acid ethyl ester (11.6 g, 23.3 mmol) in THF (500 mL) was treated with a solution LiOH (2.8 g, 116.7 mmol) in water (500 mL) at room temperature for 12 h. THF was then removed by evaporation. The mixture was then poured into ice and carefully acidified with dilute HCl to pH-1. The precipitate was collected by filtration, washed with water, and dried in vacuum to afford {tert-butyl-[3-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-benzoyl]-amino}-acetic acid as a white solid, 10.6 g (94%). LC-MS (ES) calculated for C27H27F2NO5, 483; found m/z 484 [M+H]+.

Workup

  1. customTHF was then removed by evaporation
  2. additionThe mixture was then poured into ice
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried in vacuum

Sources & evidence

ORD record
ord-15158f27018d43fe824ed7558625c1e2
Source dataset
uspto-grants-2011_10
Patent number
US08039495B2

Reaction notes

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