Triethylamine → n-butyl N-carbobenzoxy-N-[di(3-phenylpropylthio)phosphonomethyl]glycinate

HRID 224225Notes

Reaction equation

HRID 224225 reaction equation
[C:1]([N:11]([CH2:20][P:21]([O:25]Cl)([O:23]Cl)=[O:22])[CH2:12][C:13]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH2:35][SH:36])=[CH:29][CH:28]=1.C(N([CH2:42][CH3:43])CC)C>C(OCC)C>[C:1]([N:11]([CH2:20][P:21]([O:25][S:36][CH2:35][CH2:34][CH2:33][C:43]1[CH:42]=[CH:29][CH:28]=[CH:27][CH:32]=1)([O:23][S:36][CH2:35][CH2:34][CH2:33][C:30]1[CH:31]=[CH:32][CH:27]=[CH:28][CH:29]=1)=[O:22])[CH2:12][C:13]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 905963-Phenylpropane-1-thiolHCID 53954703Butyl N-carbobenzoxy-N-(dichlorophosphonomethyl)glycinate

Product 1

HCID 54157389n-butyl N-carbobenzoxy-N-[di(3-phenylpropylthio)phosphonomethyl]glycinate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

n-Butyl N-carbobenzoxy-N-(dichlorophosphonomethyl)glycinate (9.5 g., 0.24 mole) was dissolved in 150 ml. of diethyl ether. To this solution was added 3-phenylpropylthiol (7.3 g., 0.48 mole) and then triethylamine (4.8 g., 0.048 mole) dissolved in 100 ml. of diethyl ether. This mixture was then stirred for 16 hours at ambient temperature, filtered to remove the triethylamine hydrochloride, washed with a 3% solution of ammonium hydroxide and then 5% hydrochloric acid and then with brine. The ether solution was dried over sodium sulfate, filtered and then concentrated under vacuum to yield a crude product. The crude product was chromatographed on a silica gel column employing methylene chloride and diethyl ether. Concentration of the ether eluant yielded n-butyl N-carbobenzoxy-N-[di(3-phenylpropylthio)phosphonomethyl]glycinate as a light yellow oil, ND25 =1.5685 and having the following analysis.

Workup

  1. filtrationfiltered
  2. customto remove the triethylamine hydrochloride
  3. washwashed with a 3% solution of ammonium hydroxide
  4. dry with materialThe ether solution was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto yield a crude product
  8. customThe crude product was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-ffc83c2316354bdd9c154b1362a5f86a
Source dataset
uspto-grants-1980_11
Patent number
US04231782

Reaction notes

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