Acetic Acid → HCID 86593996, compound

HRID 853652Notes

Reaction equation

HRID 853652 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH:5]([O:7][P:8]([CH2:17][CH2:18][NH:19]C(OCC1C=CC=CC=1)=O)([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9])[CH3:6])[CH3:2].C(O)(=O)C>C(O)C.[Pd]>[C:4]([OH:30])(=[O:3])[CH3:5].[CH2:1]([O:3][C:4](=[O:30])[CH:5]([O:7][P:8]([CH2:17][CH2:18][NH2:19])([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9])[CH3:6])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 72466057HCID 72466057, compound

Product 1

HCID 86593996HCID 86593996, compoundYield 174.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-[(2-benzyloxycarbonylamino-ethyl)-phenoxy-phosphinoyloxy]-propionic acid ethyl ester 218 (240 mg, 0.551 mmol) with approximately 50% purity and a ratio of 2:1 of diastereomers was dissolved in 5.5 mL of ethanol with acetic acid (63 μL, 1.10 mmol). To this solution was added 36 mg of 10% Pd/C and the solution was degassed under a hydrogen atmosphere three times. The solution was vigorously stirred at room temperature for 3 hours when TLC showed complete consumption of the starting materials. The mixture was filtered through a pad of Celite and dried to provide 174 mg (87%) of 2-[(2-amino-ethyl)-phenoxy-phosphinoyloxy]-propionic acid ethyl ester; compound with acetic acid 219 as a clear oil.

Workup

  1. customthe solution was degassed under a hydrogen atmosphere three times
  2. customconsumption of the starting materials
  3. filtrationThe mixture was filtered through a pad of Celite
  4. customdried

Sources & evidence

ORD record
ord-7c28ce3aecb640748c6285c59d4ad6d5
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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