HCID 86632036, compound → GGSTOPTM

HRID 1092925Notes

Reaction equation

HRID 1092925 reaction equation
C(OC([NH:11][CH:12]([CH2:23][CH2:24][P:25]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36][C:37]([O:39]CC2C=CC=CC=2)=[O:38])[CH:31]=1)([O:27][CH3:28])=[O:26])[C:13]([O:15]CC1C=CC=CC=1)=[O:14])=O)C1C=CC=CC=1.[H][H]>CO.O.[C].[Pd]>[NH2:11][CH:12]([CH2:23][CH2:24][P:25]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36][C:37]([OH:39])=[O:38])[CH:31]=1)([O:27][CH3:28])=[O:26])[C:13]([OH:15])=[O:14]

Participants

6

Reactant 2

HCID 86632036HCID 86632036, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23582776GGSTOPTMYield 51.2%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Next, 0.72 g (1.12 mmol) of benzyl 2-(N-benzyloxycarbonylamino)-4-{[3-(benzyloxycarbonylmethyl)phenyl](methyl)phosphono}butanoate was dissolved in 24 mL of a solvent mixture of methanol and water at 5:1 and mixed with 200 mg of 5% palladium-carbon, and hydrogen gas was introduced at room temperature for 2.5 hours. Thereafter, the palladium-carbon was removed by Celite filtration and the filtrate was vacuum-concentrated and the residue was freeze-dried from water to obtain 2-amino-4-{[3-(carboxymethyl)phenyl] (methyl)phosphono}butanoic acid (0.19 g, yield 51%) as a colorless solid.

Workup

  1. additionwas introduced at room temperature for 2.5 hours
  2. customThereafter, the palladium-carbon was removed by Celite filtration
  3. concentrationthe filtrate was vacuum-concentrated
  4. dry with materialthe residue was freeze-dried from water

Sources & evidence

ORD record
ord-92fc4b3297c24ce7a37263749e250bd6
Source dataset
uspto-grants-2012_03
Patent number
US08129557B2

Reaction notes

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