Hydrochloric Acid → 2-Benzyl-3-[(1-{[(benzyloxy)carbonyl]amino}-2-phenylethyl)(hydroxy)phosphoryl]propanoic acid

HRID 1058760Notes

Reaction equation

HRID 1058760 reaction equation
[OH:1][P:2]([CH:17]([NH:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH2:4][CH:5]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]([O:8]C)=[O:7])=[O:3].[OH-].[Na+].Cl>CO>[OH:3][P:2]([CH:17]([NH:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])[CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([CH2:4][CH:5]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:6]([OH:8])=[O:7])=[O:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18668709Methyl 3-[hydroxy[2-phenyl-1-[[(phenylmethoxy)carbonyl)amino]ethyl]phosphinyl]-2-(phenylmethyl)propanoate

Product 1

HCID 186687012-Benzyl-3-[(1-{[(benzyloxy)carbonyl]amino}-2-phenylethyl)(hydroxy)phosphoryl]propanoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1 g (2.02 mmol) of methyl 3-[hydroxy[2-phenyl-1-[[(phenylmethoxy)carbonyl)amino]ethyl]phosphinyl]-2-(phenylmethyl)propanoate in 20 ml of methanol are added 20 ml of 1N sodium hydroxide. After stirring for 10 hours, the medium is acidified with 2N hydrochloric acid, the methanol is then evaporated off and the residue is extracted three times with ethyl acetate. The combined organic phases are washed with water, dried over sodium sulphate and evaporated. 0.97 g of product is recovered (yield=100%).

Workup

  1. customthe methanol is then evaporated off
  2. extractionthe residue is extracted three times with ethyl acetate
  3. washThe combined organic phases are washed with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. custom0.97 g of product is recovered (yield=100%)

Sources & evidence

ORD record
ord-a557920ddb094b44a10596349cbb5474
Source dataset
uspto-grants-2003_02
Patent number
US06518260B1

Reaction notes

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