Sodium Hydroxide → 2-(3-Aminophenyl)-3-((4-phenylbutyl)(hydroxy)phosphinoyl)propanoic acid

HRID 490939Notes

Reaction equation

HRID 490939 reaction equation
C[O:2][C:3](=[O:33])[CH:4]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH:25]C(OC(C)(C)C)=O)[CH:20]=1)[CH2:5][P:6]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([OH:8])=[O:7].[OH-].[Na+]>CO.C1COCC1.O>[NH2:25][C:21]1[CH:20]=[C:19]([CH:4]([CH2:5][P:6]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([OH:8])=[O:7])[C:3]([OH:33])=[O:2])[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 673751372-(3-(t-Butoxycarbonylamino)phenyl)-3-((4-phenylbutyl)(hydroxy)-phosphinoyl)propanoic acid methyl ester

Product 1

HCID 101261602-(3-Aminophenyl)-3-((4-phenylbutyl)(hydroxy)phosphinoyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

2-(3-(t-Butoxycarbonylamino)phenyl)-3-((4-phenylbutyl)(hydroxy)-phosphinoyl)propanoic acid methyl ester (845 mg, 1.8 mmol) was stirred in 1 M NaOH (5.3 mL, 5.3 mmol) in methanol/THF/H2O for 1.5 hours. The product was concentrated in vacuo. The residue was dissolved in 10 mL methylene chloride and TFA (10 mL) was added. After 45 minutes, the reaction mixture was concentrated to provide 2-(3-aminophenyl)-3-((4-phenylbutyl)(hydroxy)phosphinoyl)propanoic acid, NMR (DMSO-d6) 1.30-1.45 (m, 8), 1.80 (m, 1), 2.35 (m, 1), 3.62 (m, 1), 6.58-6.65 (m, 3), 7.05 (m, 1), 7.15 (m, 3), 7.23 (m, 2) ppm; as a crude product. Pure product was obtained by preparative reversed-phase HPLC.

Workup

  1. concentrationThe product was concentrated in vacuo
  2. dissolutionThe residue was dissolved in 10 mL methylene chloride
  3. additionTFA (10 mL) was added
  4. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-681a7e41f4fd473f82fdcd4dcd329911
Source dataset
uspto-grants-2009_05
Patent number
US07528173B2

Reaction notes

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