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

HRID 902933Notes

Reaction equation

HRID 902933 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 MHz: 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-33ab95bac4e0497cb3b51578e3d14f36
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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