Sodium Hydroxide → (R)-4-(biphenyl-4-yl)-3-(3-carboxypropanamido)butanoic acid

HRID 881822Notes

Reaction equation

HRID 881822 reaction equation
[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([NH:15][C:16](=[O:22])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH2:9][C:10]([O:12]CC)=[O:11])=[CH:3][CH:2]=1.[OH-].[Na+]>C1COCC1.CO>[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:2]=[CH:3][C:4]([CH2:7][C@@H:8]([NH:15][C:16](=[O:22])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 49822223(R)-4-biphenyl-4-yl-3-(3-carboxy-propionylamino)-butyric acid ethyl ester

Product 1

HCID 59607667(R)-4-(biphenyl-4-yl)-3-(3-carboxypropanamido)butanoic acidYield 96.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-4-(1-(biphenyl-4-yl)-4-ethoxy-4-oxobutan-2-ylamino)-4-oxobutanoic acid (61.2 mg, 0.160 mmol) in THF (1.6 mL) and methanol (0.2 mL), aqueous 1M NaOH solution (0.638 mL, 0.638 mmol) is added at room temperature. After stirring for 45 minutes, the reaction is quenched with aqueous 0.1 M HCl and is extracted with ethyl acetate. The organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give (R)-4-(biphenyl-4-yl)-3-(3-carboxypropanamido)butanoic acid (54.9 mg). HPLC retention time=1.33 minutes (condition A); MS (m+1)=356.1; 1H NMR (400 MHz, CD3OD) δ ppm 2.40-2.56 (m, 6 H) 2.83-2.94 (m, 2 H) 4.43-4.50 (m, 1 H) 7.29-7.32 (m, 3 H) 7.41 (t, 2 H, J=7.7 Hz) 7.53-7.60 (m, 4 H).

Workup

  1. customthe reaction is quenched with aqueous 0.1 M HCl
  2. extractionis extracted with ethyl acetate
  3. washThe organic layer is washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0ed18c4fe0c44f5b97536b74e4931e03
Source dataset
uspto-grants-2015_03
Patent number
US08993631B2

Reaction notes

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