Hydrochloric Acid → 4-[(4-{(1RS,2SR)-2-[(6,7-dihydro-5H-benzo[a][7]annulen-1-ylcarbonyl)amino]-1-hydroxy-3-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]propyl}phenoxy)methyl]benzoic acid

HRID 1610580Notes

Reaction equation

HRID 1610580 reaction equation
[C:1]1([C:12]([NH:14][CH:15]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([O:43][C:44]([F:49])([F:48])[CH:45]([F:47])[F:46])[CH:38]=2)[CH:16]([C:18]2[CH:35]=[CH:34][C:21]([O:22][CH2:23][C:24]3[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[OH:17])=[O:13])[C:6]2[CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>CO>[C:1]1([C:12]([NH:14][CH:15]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([O:43][C:44]([F:48])([F:49])[CH:45]([F:46])[F:47])[CH:38]=2)[CH:16]([C:18]2[CH:35]=[CH:34][C:21]([O:22][CH2:23][C:24]3[CH:33]=[CH:32][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[OH:17])=[O:13])[C:6]2[CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22261395methyl 4-[(4-{(1RS,2SR)-2-[(6,7-dihydro-5H-benzo[a][7]annulen-1-ylcarbonyl)amino]-1-hydroxy-3-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]propyl}phenoxy)methyl]-benzoate

Product 1

HCID 222617964-[(4-{(1RS,2SR)-2-[(6,7-dihydro-5H-benzo[a][7]annulen-1-ylcarbonyl)amino]-1-hydroxy-3-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]propyl}phenoxy)methyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 4-[(4-{(1RS,2SR)-2-[(6,7-dihydro-5H-benzo[a][7]annulen-1-ylcarbonyl)amino]-1-hydroxy-3-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]propyl}phenoxy)methyl]-benzoate (260 mg, 0.384 mmol) in methanol (10 ml) was added 2N aqueous sodium hydroxide solution (0.38 ml, 0.76 mmol), and the mixture was stirred at 60° C. overnight. The reaction solution was acidified with 1N hydrochloric acid and extracted with ethyl acetate (100 ml×2). The extract was washed with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. Recrystallization of the residue from ethyl acetate-hexane gave the objective substance (209 mg, 82%).

Workup

  1. extractionextracted with ethyl acetate (100 ml×2)
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. customevaporated under reduced pressure
  5. customRecrystallization of the residue from ethyl acetate-hexane
  6. customgave the objective substance (209 mg, 82%)

Sources & evidence

ORD record
ord-9c421521c4514c4f91293460a23cd480
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

Loading…