Hydrochloric Acid → ethyl N-carbobenzoxy-N-(dichlorophosphonomethyl)glycinate

HRID 903006Notes

Reaction equation

HRID 903006 reaction equation
C(N(CP(O)(O)=O)CC(O)=O)C.[Cl:13]C(OCC1C=CC=CC=1)=O.C(=O)([O-])[O-].[Na+].[Na+].[ClH:30].[C:31]([N:41]([CH2:48][P:49]([OH:52])([OH:51])=[O:50])[CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32]>O>[C:31]([N:41]([CH2:48][P:49]([O:51][Cl:13])([O:52][Cl:30])=[O:50])[CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:32]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformate2×HCID 15029720Ethyl N-phosphonomethylglycineHCID 23337289ehtyl N-carbobenzoxy-N-phosphonomethylglycinate

Product 1

HCID 54297302ethyl N-carbobenzoxy-N-(dichlorophosphonomethyl)glycinate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl N-phosphonomethylglycine (9.85 g., 0.05 mole) and benzyl chloroformate (9.4 g., 0.05 mole) were dissolved in 50 ml. of water and sodium carbonate (7.95 g., 0.075 mole) was added over a 1/2 hour period. The solution was stirred until all of the benzyl chloroformate had reacted. Concentrated hydrochloric acid (12.5 ml) was then added. Upon standing ethyl N-carbobenzoxy-N-phosphonomethylglycinate separated as an oil. The oil was then dried in a vacuum dessicator over phosphorus pentoxide at 0.55 torr. A 4 g. sample of the oil was dissolved in oxalyl chloride (20 ml) and stirred until gas evolution ceased. The mixture was concentrated in vacuo to yield ethyl N-carbobenzoxy-N-(dichlorophosphonomethyl)glycinate as a colorless oil. The oil is treated with an excess of oxalyl chloride to convert it to ethyl N-carbobenzoxy-N-phosphonomethylglycine dichloride which is then reacted with the appropriate thiol of the formula

Workup

  1. customhad reacted
  2. customseparated as an oil
  3. dry with materialThe oil was then dried in a vacuum dessicator over phosphorus pentoxide at 0.55 torr
  4. dissolutionsample of the oil was dissolved in oxalyl chloride (20 ml)
  5. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-c93de37adc104491bf9b34584ba87a7a
Source dataset
uspto-grants-1980_10
Patent number
US04226611

Reaction notes

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