Hydrogen Bromide → HCID 86737080, compound

HRID 2057495Notes

Reaction equation

HRID 2057495 reaction equation
C([CH:3]([C:24]([OH:26])=[O:25])[N:4]([CH2:15][P:16]([S:21][CH2:22][CH3:23])([S:18][CH2:19][CH3:20])=[S:17])[C:5](OCC1C=CC=CC=1)=O)C.Br.[CH3:28]COCC>C(O)(=O)C>[CH2:5]([N:4]([CH2:15][P:16]([S:21][CH2:22][CH3:23])([S:18][CH2:19][CH3:20])=[S:17])[CH2:3][C:24]([OH:26])=[O:25])[CH3:28]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 20330629HCID 20330629, compound

Product 1

HCID 86737080HCID 86737080, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl-N-[bis(ethylthio)phosphinothioylmethyl]-N-(benzyloxycarbonyl)glycine (4.0 g.) was dissolved in 10 ml. of 35% hydrobromic acid in acetic acid and stirred for one hour. Ether was then added to precipitate the desired material as the hydrobromide salt. The residue was washed three additional times with ether. The residue was then dissolved in benzene and treated with excess propylene oxide. The propylene oxide-benzene solution was then concentrated in vacuo to yield a yellow oil (1.5 g.) which was chromatographed on fluorosil with diethyl ether as an eluant to yield ethyl-N-[bis(ethylthio)phosphinothioylmethyl]glycine as an oil, ND25 =1.582.

Workup

  1. customto precipitate the desired material as the hydrobromide salt
  2. washThe residue was washed three additional times with ether
  3. dissolutionThe residue was then dissolved in benzene
  4. additiontreated with excess propylene oxide
  5. concentrationThe propylene oxide-benzene solution was then concentrated in vacuo
  6. customto yield a yellow oil (1.5 g.) which
  7. customwas chromatographed on fluorosil with diethyl ether as an eluant

Sources & evidence

ORD record
ord-6bd6d0dd89834860b924dbcc201d2be9
Source dataset
uspto-grants-1980_07
Patent number
US04211548

Reaction notes

Loading…