Hydrogen Bromide → HCID 88776574, compound

HRID 903012Notes

Reaction equation

HRID 903012 reaction equation
C([CH:3]([C:26]([OH:28])=[O:27])[N:4]([C:16](OCC1C=CC=CC=1)=O)[CH2:5][P:6]([CH2:12][CH:13]([CH3:15])[CH3:14])([CH2:8][CH:9]([CH3:11])[CH3:10])=[S:7])C.Br.[CH3:30]COCC>C(O)(=O)C>[CH2:16]([N:4]([CH2:5][P:6]([CH2:12][CH:13]([CH3:15])[CH3:14])([CH2:8][CH:9]([CH3:11])[CH3:10])=[S:7])[CH2:3][C:26]([OH:28])=[O:27])[CH3:30]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 131711907HCID 131711907, compound

Product 1

HCID 88776574HCID 88776574, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl N-carbobenzoxy-N-(diisobutylthiophosphinylmethyl)glycine (4 g., 0.009 mole) was dissolved in 10 ml. of 35% hydrogen bromide in glacial acetic acid at 0° C. The mixture was stirred for one hour. Ether was added and the oily precipitate isolated by decanting the ether layer. The oil was washed twice with diethyl ether and then suspended in benzene and treated with propylene oxide. The solution was concentrated in vacuo to yield ethyl N-(diisobutylthiophosphinylmethyl)glycine (0.3 g., 0.001 mole) as an oil, ND25 =1.5121.

Workup

  1. customat 0° C
  2. customthe oily precipitate isolated
  3. customby decanting the ether layer
  4. washThe oil was washed twice with diethyl ether
  5. additiontreated with propylene oxide
  6. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-de1cd023f7654fd6a72dd32fbbe7fb97
Source dataset
uspto-grants-1980_10
Patent number
US04226611

Reaction notes

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