Lithium Hydroxide → 3-[Benzyl(hydroxy)phosphoryl]-2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)propanoic acid

HRID 2223239Notes

Reaction equation

HRID 2223239 reaction equation
[CH2:1]([P:8]([CH2:11][CH:12]([CH2:18][C:19]1[CH:20]=[N:21][C:22]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:23][CH:24]=1)[C:13]([O:15]CC)=[O:14])(=[O:10])[OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.O>[CH2:1]([P:8]([CH2:11][CH:12]([CH2:18][C:19]1[CH:20]=[N:21][C:22]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:23][CH:24]=1)[C:13]([OH:15])=[O:14])([OH:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68804398Benzyl[2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-3-ethoxy-3-oxopropyl]phosphinic acid

Product 1

HCID 688023693-[Benzyl(hydroxy)phosphoryl]-2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)propanoic acidYield 81.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Benzyl[2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-3-ethoxy-3-oxopropyl]phosphinic acid (62 mg; 0.13 mmol) was dissolved in THF (1 mL) and water (1 mL). LiOH (12 mg; 0.5 mmol) was added, and the reaction was stirred at room temperature overnight. The reaction mixture was concentrated, water (1 mL) was added and the aqueous solution was extracted with CHCl3 (1×1 mL). 0.5 M aqueous HCl (1 mL) was added to the aqueous solution, and the resulting acidic aqueous solution was extracted with CHCl3 (3×2 mL). The combined organic phases were dried and concentrated to afford 46 mg (81%) of 3-[benzyl(hydroxy)phosphoryl]-2-({6-[(tert-butoxycarbonyl)amino]-pyridin-3-yl}methyl)propanoic acid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater (1 mL) was added
  3. extractionthe aqueous solution was extracted with CHCl3 (1×1 mL)
  4. addition0.5 M aqueous HCl (1 mL) was added to the aqueous solution
  5. extractionthe resulting acidic aqueous solution was extracted with CHCl3 (3×2 mL)
  6. customThe combined organic phases were dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1d389740fd254aee99f31903b9e7c315
Source dataset
uspto-grants-2008_05
Patent number
US07375121B2

Reaction notes

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