171922-16-0

Basic information

• Product Name: 4-Pentynoic acid, 2-[(diphenylmethylene)amino]-, ethyl ester
• CAS NO: 171922-16-0
• Molecular Formula: C20H19NO2
• Molecular Weight: 305.376
• Mol File: 171922-16-0.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: 4-Pentynoic acid, 2-[(diphenylmethylene)amino]-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pentynoic acid, 2-[(diphenylmethylene)amino]-, ethyl ester(171922-16-0)
• EPA Substance Registry System: 4-Pentynoic acid, 2-[(diphenylmethylene)amino]-, ethyl ester(171922-16-0)

Safety Data

• Hazardous Substances Data: 171922-16-0(Hazardous Substances Data)

Upstream product

• 69555-14-2 ethyl N-diphenylmethylene glycine 
• 106-96-7 propargyl bromide 
• 624-65-7 2-propynyl chloride 
• 6165-75-9 propargyl benzenesulfonate 
• 1013-88-3 Benzophenone imine 

Downstream Products

• 1226781-44-7 Omarigliptin 
• 1226781-87-8 tert-butyl {(2R,3S,5R)-2-(2,5-difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-yl}carbamate 
• 951127-25-6 N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester 
• 1172623-99-2 tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbamate 
• 271598-92-6 ethyl 2-{[(4-methylphenyl)sulfonyl]amino}pent-4-ynoate 
• 293755-92-7 ethyl 2-{[(4-methylphenyl)sulfonyl](3-trimethylsilylprop-2-ynyl)amino}pent-4-ynoate 
• 293755-93-8 ethyl 2-{[(4-methylphenyl)sulfonyl](prop-2-ynyl)amino}pent-4-ynoate 
• 207294-54-0 ethyl 1-acetamido-3-cyclopentene-3-vinyl-1-carboxylate 
• 499797-06-7 3-acetoxymethyl-5-[2-(2,2-dimethyl-propionylamino)-2-ethoxycarbonyl-ethyl]-cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester 
• 499797-05-6 3-acetoxymethyl-5-(2-acetylamino-2-ethoxycarbonyl-ethyl)-cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester 
• 23235-05-4 L,D-acetylpropargylglycine ethyl ester 
• 171922-32-0 ethyl 2-allyl-N-(diphenylmethylene)-2-propargylglycinate 
• 1172623-96-9 (±)-tert-butyl (1-(2,5-difluorophenyl)-1-oxopent-4-yn-2-yl)carbamate 

Relevant articles and documents

Solid-phase synthesis of novel heterocycles containing thiohydantoin and isoxazole rings

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An uncatalyzed cyclo-elimination process for the release of N3- alkylated hydantoins from solid-phase: Synthesis of novel isoxazoloimidazolidinediones

Solid-phase regioselective nitrile oxide 1,3-dipolar cycloaddition to an ω-alkynyl ester followed by reductive α-N-alkylation and isocyanate α-N- acylation delivers I and sets the stage for the uncatalyzed carbanilide cycloelimination of isoxazoloimidazolidinedione heterocycles (I → II). This traceless release step is induced by simply warming the urea ester intermediate, but requires that the N3 of the nascent hydantoin be fully substituted (I → II; R(c) ≠ H).

Evolution of a Manufacturing Route to Omarigliptin, A Long-Acting DPP-4 Inhibitor for the Treatment of Type 2 Diabetes

Development of a convergent synthesis of omarigliptin (MK-3102) suitable for commercial manufacture is described. The target molecule is assembled through a diastereoselective reductive amination of a highly functionalized pyranone with a mesylated pyrazole followed by deprotection of a Boc group. The synthesis of the pyranone relies on three Ru-catalyzed reactions: (1) a DKR reduction of a rac-α-aminoketone to set the two contiguous stereogenic centers, (2) a cycloisomerization of a bis-homopropargylic alcohol to a dihydropyran, and, finally, (3) a Ru-catalyzed oxidation of a pyranol to the desired pyranone. The regioselective synthesis of a N-Boc-1-mesyl pyrazole fragment was achieved via base-promoted mesyl group isomerization to afford 30:1 selectivity. A highlight of the endgame process development is telescoping a Boc deprotection and reductive amination followed by direct crystallization of the penultimate from the reaction mixture. This avoids handling of an unstable, mutagenic 1-mesylpyrazole BSA salt used in the earlier multikilogram deliveries and improves the overall diastereoselectivity and efficiency of the route.

Process for preparing Chiral Dipeptidyl Peptidase -IV Inhibitor Intermediates

A novel process is provided for the preparation of chiral trans-2,3-disubstituted 5-oxotetrahydropyrans of structural formula (I): wherein Ar is optionally substituted phenyl and P is a primary amine protecting group. These compounds are useful in the synthesis of dipeptidyl peptidase-IV inhibitors for the treatment of Type 2 diabetes. Also provided are useful intermediates obtained from the process.