Sodium Hydroxide → 3-(2-Biphenyl-4-yl-ethylcarbamoyl)-pentandioic acid mono-tert-butyl ester

HRID 2214261Notes

Reaction equation

HRID 2214261 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][CH:6]([C:15](=[O:31])[NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])C.[OH-].[Na+]>CO>[C:11]([O:10][C:8](=[O:9])[CH2:7][CH:6]([C:15](=[O:31])[NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)[CH2:5][C:4]([OH:32])=[O:3])([CH3:14])([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 692126363-(2-Biphenyl-4-yl-ethylcarbamoyl)-pentanedioic acid tert-butyl ester ethyl ester

Product 1

HCID 692127343-(2-Biphenyl-4-yl-ethylcarbamoyl)-pentandioic acid mono-tert-butyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the compound of example 71 (1.09 g, 2.48 mmol) in methanol (50 mL) was added drop wise a sodium hydroxide solution (1N, 5 mL, 5 mmol). After stirring the reaction mixture for 24 h, the solvent was evaporated. The residue was partitioned between water and ether. The aqueous phase was acidified with concentrated HCl, and then extracted with ethyl acetate. The organic phase was washed with brine, dried, filtered and evaporated to give the product as a white solid. 1H-NMR(CDCl3, 400 MH: 1.37(s, 9H); 2.28–2.61(m, 4H); 2.79(t, J=7.3 Hz, 2H); 3.08(m, 1H); 3.27(m, 1H); 3.39 (m, 2H); 6.25(m, t, 5.1 Hz, 1H); 7.26(m, 3H); 7.36(m, 2H); 7.52(m, 4H).

Workup

  1. customthe solvent was evaporated
  2. customThe residue was partitioned between water and ether
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-4280b5a8fb0e4cc9a24e45dd1c0e2f3b
Source dataset
uspto-grants-2006_09
Patent number
US07105539B2

Reaction notes

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