74743-61-6

Basic information

• Product Name: (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
• Synonyms: (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
• CAS NO: 74743-61-6
• Molecular Weight: 330.408
• Mol File: 74743-61-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (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(CAS DataBase Reference)
• NIST Chemistry Reference: (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(74743-61-6)
• EPA Substance Registry System: (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(74743-61-6)

Safety Data

• Hazardous Substances Data: 74743-61-6(Hazardous Substances Data)

Upstream product

• 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 
• 74-88-4 methyl iodide 
• 63267-97-0 (3S)-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 
• 52512-70-6 (S)-2-((1S)-3-benzyl-7-oxo-(1rH,5cH)-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-mercapto-3-methyl-butyric acid; mercury(II) salt (1:1) 

Downstream Products

• 92541-78-1 (3R)-3-amino-3,4,4-trimethylthietan-2-one toluene-p-sulphonate 
• 92462-78-7 (2S)-2-amino-2,3-dimethyl-3-mercaptobutanoic acid toluene-p-sulphonate 
• 92462-86-7 (4S)-4,5,5-trimethylthiazolidine-4-carboxylic acid toluene-p-sulphonate 
• 4283-15-2 phenylacetylcarbamic acid ethyl ester 
• 92462-75-4 (3R)-3-(2-benzyl-5-oxo-2-oxazolin-4-ylidene)amino-3,4,4-trimethylthietan-2-one 
• 92462-73-2 (3R)-3-(2-benzyloxazol-5-ylcarbonyl)amino-3,4,4-trimethylthietan-2-one 
• 103-82-2 phenylacetic acid 
• 6000-43-7 2-aminoethanoic acid hydrochloride 
• 88168-76-7 (2-RS)-2-amino-3-mercapto-2,3-dimethylbutanoic acid hydrochloride 

Relevant articles and documents

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).