4283-15-2

Upstream product

• 64-17-5 ethanol 
• 51-79-6 urethane 
• 103-80-0 phenylacetyl chloride 
• 92462-79-8 (3S)-3-(2-benzyl-5-oxo-2-oxazolin-4-ylidene)amino-3,4,4-trimethylthietan-2-one 
• 92462-75-4 (3R)-3-(2-benzyl-5-oxo-2-oxazolin-4-ylidene)amino-3,4,4-trimethylthietan-2-one 
• 122-52-1 triethyl phosphite 
• 60-29-7 diethyl ether 
• 101-97-3 Ethyl 2-phenylethanoate 
• 74743-62-7 (3S)-3-<(1S,5R)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-3,4,4-trimethylthietan-2-one 
• 74743-61-6 (3R)-3-<(1S,5R)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-3,4,4-trimethylthietan-2-one 
• 63212-16-8 (3R)-3-<(1S,5R)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-4,4-dimethylthietan-2-one 
• 25289-32-1 Phenyl-prop-2-ynoyl azide 

Downstream Products

• 5330-40-5 bis-phenylacetyl-amine 
• 103-81-1 Benzeneacetamide 
• 108-80-5 isocyanuric acid 
• 5465-00-9 N-ethylphenylacetamide 
• 3538-62-3 N-ethyl-N'-phenylacetyl-urea 
• 103-82-2 phenylacetic acid 
• 63-98-9 phenacemide 
• 4898-52-6 2-phenyl-N-(phenylcarbamoyl)acetamide 
• 621-06-7 2,N-diphenylacetamide 
• 603-54-3 N,N-diphenylurea 

Relevant academic research and scientific papers

ORGANOPHOSPHORUS COMPOUNDS XXXIX. THE ACTION OF ALKYL PHOSPHITES ON OXAZOLIDINEDIONES. A NOVEL SYNTHESIS OF CARBAMIC ACID DERIVATIVES

Depending upon the experimental conditions trimethyl-, triethyl-, and triisopropyl phosphites react with oxazolidinedione (1a) ti give acid 2a and/or the corresponding alkyl ester 2b, c.Phenylacetamide (3) is also formed in a small amount.On the other hand, trialkyl phosphites cause the quantitative conversion of dione 1b into diphenylacetamide.The identity of the new compounds is established from analytical, chemical and spectroscopic evidence.

Studies Related to Thietan-2-ones. Part 2. Conversion of a Benzylpenicillin-derived Thietan-2-one into D- and L-2-Methylpenicillamines

(3R)- and (3S)-hept-2-en-6-yl>-3,4,4-trimethylthietan-2-ones (8b) and (9b) were isomerised to (3R)- and (3S)-3-(2-benzyloxazol-5-ylcarbonyl)amino-3,4,4-trimethylthietan-2-ones (10) and (14) by m-chlorobenzoic acid in methanol.Attempts to cleave the amide linkage of compound (10), by the action of phosphorus(V) chloride-methanol, were unrewarding.In dichloromethane containing boron trifluoride, compound (8b) was converted into (3R)-3-(2-benzyl-5-oxo-2-oxazolin-4-ylidene)amino-3,4,4-trimethylthietan-2-one (16).Ozonolysis of the lastmentioned compound in dichloromethane at -78 deg C and addition of ethanol yielded (3R)-3-(formyl)amino-3,4,4-trimethylthietan-2-one (17) and N-(ethoxycarbonyl)phenylacetamide (22a).Removal of the formyl group from compound (17) was achieved by the action of phosphorus(V) trichloride oxide-methanol to give, following addition of toluene-p-sulphonic acid, (3R)-3-amino-3,4,4-trimethylthietan-2-one toluene-p-sulphonate (4c).In boiling water, the thietanone (4c) underwent hydrolysis to give (2S)-2-amino-2,3-dimethyl-3-mercaptobutanoic acid toluene-p-sulphonate (D-2-methylpenicillamine toluene-p-sulphonate) (27b).Using a similar reaction sequence, the thietanone (9b) was transformed into L-2-methylpenicillamine toluene-p-sulphonate (28b).D-Penicillamine toluene-p-sulphonate (27a) underwent thiazolidine formation with formaldehyde more rapidly than did compound (27b).