Acetic Acid → HCID 86737083, compound

HRID 2057499Notes

Reaction equation

HRID 2057499 reaction equation
C([CH:3]([C:28]([OH:30])=[O:29])[N:4]([CH2:15][P:16]([S:23][CH2:24][CH2:25][CH2:26][CH3:27])([S:18][CH2:19][CH2:20][CH2:21][CH3:22])=[S:17])[C:5](OCC1C=CC=CC=1)=O)C.Br.[C:32](O)(=O)C>>[CH2:5]([N:4]([CH2:15][P:16]([S:23][CH2:24][CH2:25][CH2:26][CH3:27])([S:18][CH2:19][CH2:20][CH2:21][CH3:22])=[S:17])[CH2:3][C:28]([OH:30])=[O:29])[CH3:32]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 20330652HCID 20330652, compound

Product 1

HCID 86737083HCID 86737083, compound

Procedure

Ethyl-N-[bis(n-butylthio)phosphinothioylmethyl]-N-(benzyloxycarbonyl)glycine (3.1 g.) was dissolved in 15 ml. of 35% hydrobromic acid in acetic acid and stirred for two hours. The solvent was then removed under reduced pressure and the residue triturated four times with diethyl ether. The residue was then dissolved in benzene, treated with excess propylene oxide and concentrated to a viscous oil. The viscous oil was chromatographed on silica gel employing dichloromethane to yield ethyl-N-[bis(n-butylthio)phosphinothioylmethyl]glycine as an oil, ND25 =1.4835.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe residue triturated four times with diethyl ether
  3. dissolutionThe residue was then dissolved in benzene
  4. additiontreated with excess propylene oxide
  5. concentrationconcentrated to a viscous oil
  6. customThe viscous oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-c98da761d46c42f5bf2acae91723eaa8
Source dataset
uspto-grants-1980_07
Patent number
US04211548

Reaction notes

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