Hydrochloric Acid → {[3-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-benzoyl]-methyl-amino}-acetic acid

HRID 1665254Notes

Reaction equation

HRID 1665254 reaction equation
C([O:3][C:4](=[O:34])[CH2:5][N:6]([C:8](=[O:33])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:24]=3[O:31][CH3:32])=[CH:19][CH:18]=2)[CH:10]=1)[CH3:7])C.[Li+].[OH-].Cl>O1CCOCC1.O>[F:30][C:26]1[C:27]([F:29])=[CH:28][C:23]([C:20]2[CH:21]=[CH:22][C:17]([O:16][CH2:15][C:11]3[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=3)[C:8]([N:6]([CH2:5][C:4]([OH:34])=[O:3])[CH3:7])=[O:33])=[CH:18][CH:19]=2)=[C:24]([O:31][CH3:32])[CH:25]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67152371{[3-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-benzoyl]-methyl-amino}-acetic acid ethyl ester

Product 1

HCID 52933306{[3-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-benzoyl]-methyl-amino}-acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of {[3-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-benzoyl]-methyl-amino}-acetic acid ethyl ester (17 g, 36 mmol) in dioxane (400 mL) was treated with a solution of LiOH (4.4 g, 180 mmol) in water (400 mL) at room temperature for 12 h, followed by acidification with dilute HCl to pH-2-4. The mixture was extracted with ethyl acetate (3 times). The combined layer was washed with water and brine, dried over sodium sulfate, filtered, and evaporated to give {[3-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-benzoyl]-methyl-amino}-acetic acid as an off-white solid, 13.5 g (85%), after drying in high vacuum at 60° C. for 48 h. LC-MS (ES) calculated for C26H25F2NO5, 441; found m/z 442 [M+H]+.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3 times)
  2. washThe combined layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-8d58c83f014b48ddbdc4cc908b0b58ae
Source dataset
uspto-grants-2011_10
Patent number
US08039495B2

Reaction notes

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