Hydrogen Bromide → HCID 86737079, compound

HRID 2057494Notes

Reaction equation

HRID 2057494 reaction equation
C([CH:3]([C:22]([OH:24])=[O:23])[N:4]([CH2:15][P:16]([S:20][CH3:21])([S:18][CH3:19])=[S:17])[C:5](OCC1C=CC=CC=1)=O)C.Br.[CH3:26]COCC>C(O)(=O)C>[CH2:5]([N:4]([CH2:15][P:16]([S:20][CH3:21])([S:18][CH3:19])=[S:17])[CH2:3][C:22]([OH:24])=[O:23])[CH3:26]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 20330641HCID 20330641, compound

Product 1

HCID 86737079HCID 86737079, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl-N-[bis(methylthio)phosphinothioylmethyl]-N-(benzyloxycarbonyl)glycine (5.9 g.) was dissolved in 11 ml. of 35% hydrobromic acid in acetic acid and stirred for one hour. Ether was added to the reaction solution which precipitated ethyl-N-[bis(methylthio)phosphinothioylmethyl]glycine hydrobromide salt as an oily liquid. This oil was washed three more times with additional ether. The material was suspended in benzene and treated with propylene oxide which effected almost complete solution. The solution was then concentrated to an oil at 0.5 torr. The oil thus recovered was chromatographed on 25 g. of silica gel employing diethyl ether as the eluant to yield ethyl-N-[bis(methylthio)phosphinothioylmethyl]glycine (1.46 g.) as an oil, ND25 =1.6002.

Workup

  1. customprecipitated ethyl-N-[bis(methylthio)phosphinothioylmethyl]glycine hydrobromide salt as an oily liquid
  2. washThis oil was washed three more times with additional ether
  3. additiontreated with propylene oxide which
  4. concentrationThe solution was then concentrated to an oil at 0.5 torr
  5. customThe oil thus recovered
  6. customwas chromatographed on 25 g

Sources & evidence

ORD record
ord-1a1626e70dd641bcbdc642555538b10d
Source dataset
uspto-grants-1980_07
Patent number
US04211548

Reaction notes

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