Phosphorous acid → HCID 131714758, compound

HRID 1982628Notes

Reaction equation

HRID 1982628 reaction equation
[CH3:1][CH:2]([CH3:26])[CH2:3][C@H:4]([NH:15]C(OCC1C=CC=CC=1)=O)[CH2:5][NH:6][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].P(O)(O)O>CO.[Pd].CCOCC>[NH2:15][C@@H:4]([CH2:3][CH:2]([CH3:26])[CH3:1])[CH2:5][NH:6][CH2:7][C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9]

Participants

6

Reactant 2

HCID 107909Phosphorous acidHCID 57212661HCID 57212661, compound

Product 1

HCID 131714758HCID 131714758, compoundYield 93.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 17.43 g of (S)-N-[4-methyl-2-[[(phenylmethoxy)carbonyl]amino]pentyl]glycine, 1,1-dimethylethyl ester in 150 ml of methanol is reduced at 25°, 50 psi using 1 g of 20% palladium on carbon as the catalyst. The filtered solution is treated with 7.84 g of phosphorous acid in 10 ml of ether and the solvent removed under reduced pressure. The residue is partitioned between ether and 10% sodium hydroxide. The aqueous phase is washed five times with ether and the combined ether washes are washed with saturated sodium chloride solution and dried over magnesium sulfate. Removal of the solvent under reduced pressure at 25° gives 10.28 g of crude (S)-N-(2-amino-4-methylpentyl)-glycine, 1,1-dimethylethyl ester. The crude product is sufficiently pure for use in subsequent reactions.

Workup

  1. customis reduced at 25°
  2. customthe solvent removed under reduced pressure
  3. customThe residue is partitioned between ether and 10% sodium hydroxide
  4. washThe aqueous phase is washed five times with ether
  5. washthe combined ether washes are washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of the solvent under reduced pressure at 25°

Sources & evidence

ORD record
ord-5e788287300d4375b47e974c2666d57a
Source dataset
uspto-grants-1986_06
Patent number
US04596819

Reaction notes

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