HCID 53730197, compound → HCID 54067144, compound

HRID 1003274Notes

Reaction equation

HRID 1003274 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:19][CH2:20][CH2:21][CH2:22][C:23]([O:25]CC)=[O:24])=[CH:14][CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.C(O)C.[OH-].[Na+]>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:14][CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 53730197HCID 53730197, compound

Product 1

HCID 54067144HCID 54067144, compoundYield 99.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Ethyl (s)-4-[2-(tert-butoxycarbonylamino)-1,2,3,4-tetra-hydronaphthalen-7-yloxy]butyrate (988 mg) was dissolved in a mixed solvent of methanol (15 ml) and ethanol (15 ml), and 2N aqueous sodium hydroxide solution (3.0 ml) was added to the solution at room temperature with stirring. After reaction for 2 hours, the reaction mixture was concentrated in vacuo. To the resulting residue was added 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to give (S)-4-[2-(tert-butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yloxy]butyric acid (914 mg) having a melting point of 150-153° C.

Workup

  1. additionwas added to the solution at room temperature
  2. customAfter reaction for 2 hours
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. additionTo the resulting residue was added 10% aqueous citric acid solution
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5fc4caa8960346e2b251f910ba5d3695
Source dataset
uspto-grants-2000_04
Patent number
US06046192

Reaction notes

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