Sodium Hydroxide → HCID 21466074, compound

HRID 1940386Notes

Reaction equation

HRID 1940386 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[S:14][C:15]([C:17]([NH:19][CH2:20][CH2:21][C:22]3[CH:34]=[CH:33][C:25]([O:26][CH2:27][C:28]([O:30]CC)=[O:29])=[CH:24][CH:23]=3)=[O:18])=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[S:14][C:15]([C:17]([NH:19][CH2:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]([O:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:33][CH:34]=3)=[O:18])=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21466033HCID 21466033, compound

Product 1

HCID 21466074HCID 21466074, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of the compound prepared in (a) (250 mg) in ethanol was added 1N sodium hydroxide (2.6 ml), and the mixture was stirred under ice-cooling for 3 hours. After the reaction mixture was concentrated under reduced pressure, ethyl acetate and water were added. The mixture was acidified with 1N hydrochloric acid. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 214 mg of 4-[2-[[(5-t-butoxycarbonyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)carbonyl]amino]ethyl]phenoxyacetic acid (yield, 91%).

Workup

  1. temperaturecooling for 3 hours
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure, ethyl acetate and water
  3. additionwere added
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9d1f408f8ed045e0af07cb1cd5bb780c
Source dataset
uspto-grants-1997_12
Patent number
US05698692

Reaction notes

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