Sodium Hydroxide → (S)-4-(biphenyl-4-yl)-3-[(dimethylphosphonomethyl)-amino]-butyric acid

HRID 1078681Notes

Reaction equation

HRID 1078681 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][C@@H:5]([NH:19][CH2:20][P:21]([O:25][CH3:26])([O:23][CH3:24])=[O:22])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.[OH-].[Na+]>CO>[C:10]1([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:9]=[CH:8][C:7]([CH2:6][C@H:5]([NH:19][CH2:20][P:21]([O:25][CH3:26])([O:23][CH3:24])=[O:22])[CH2:4][C:3]([OH:27])=[O:2])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54030507(S)-4-(biphenyl-4-yl)-3-[(dimethylphosphonomethyl)-amino]-butyric acid methyl ester

Product 1

HCID 53781905(S)-4-(biphenyl-4-yl)-3-[(dimethylphosphonomethyl)-amino]-butyric acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-4-(biphenyl-4-yl)-3-[(dimethylphosphonomethyl)-amino]-butyric acid methyl ester (851 mg, 2.26 mmol) in methanol (2 mL) is added 2N sodium hydroxide (1.5 mL, 3 mmol). After 1 hour of stirring, methanol is removed under vacuum and water (5 mL) is added to the residue. The aqueous layer is washed with ethyl acetate (10 mL), then acidified with 1N hydrochloric acid (4 mL). The residue is extracted with ethyl acetate (2×10 mL) and methylene chloride (10 mL). The combined organic layers are dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to yield (S)-4-(biphenyl-4-yl)-3-[(dimethylphosphonomethyl)-amino]-butyric acid as a gummy solid.

Workup

  1. custommethanol is removed under vacuum and water (5 mL)
  2. additionis added to the residue
  3. washThe aqueous layer is washed with ethyl acetate (10 mL)
  4. extractionThe residue is extracted with ethyl acetate (2×10 mL) and methylene chloride (10 mL)
  5. dry with materialThe combined organic layers are dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1aee31de9cd84ae18669dfceb0d38627
Source dataset
uspto-grants-1996_08
Patent number
US05550119

Reaction notes

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