131971-66-9

Upstream product

• 6117-91-5 (E/Z)-2-buten-1-ol 
• 216959-34-1 ethyl 2-{[(tert-butoxy)carbonyl]amino}-2-oxoacetate 
• 56930-04-2 trans-crotylamine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 155055-38-2 1-[bis-N-(tert-butoxycarbonyl)amino]-but-2-yne 
• 51779-32-9 iminodicarboxylic acid di-tert-butyl ester 
• 590-18-1 (Z)-2-Butene 
• 78888-18-3 N-tert-butoxycarbonylprop-2-en-1-amine 
• 115270-01-4 1--2(E)-butene 
• 156731-36-1 1-(N-tert-butoxycarbonylamino)-but-2-yne 
• 1401981-68-7 N-(phenylmethoxy)-N-2-butenylcarbamic acid 1,1-dimethylethyl ester 
• 79722-21-7 tert-butyl N-(benzyloxy)carbamate 

Downstream Products

• 1379538-60-9 N-tert-butoxycarbonyl-4-methyl-3-phenyl-1,4-dihydropyridine 
• 1379538-78-9 (E)-N-(but-2-en-1-yl)-N-tert-butoxycarbonyl-phenylethynylamine 
• 171920-16-4 (E)-N-tert-Butoxycarbonyl-N-but-2-enylbenzylamine 
• 56930-04-2 trans-crotylamine 

Relevant academic research and scientific papers

N-Methyl Allylic Amines from Allylic Alcohols by Mitsunobu Substitution Using N-Boc Ethyl Oxamate

We report the practical, scalable synthesis of a range of N-methyl allylic amines. Primary and secondary allylic alcohols underwent a regioselective Mitsunobu reaction with readily accessible N-Boc ethyl oxamate to deliver the corresponding N-Boc allylic amines, including in enantiopure form via stereospecific substitution. Subsequent N-methylation and Boc deprotection without chromatography yielded the amine products as hydrochloride salts. This method solves the problem of converting commercially available alcohols into often volatile N-methyl allylic amines, many of which have limited commercial availability.

Enantioselective and Regiodivergent Functionalization of N-Allylcarbamates by Mechanistically Divergent Multicatalysis

A pair of mechanistically divergent multicatalytic reaction sequences has been developed consisting of nickel-catalyzed isomerization of N-allylcarbamates and subsequent phosphoric-acid-catalyzed enantioselective functionalization of the resulting intermediates. By appropriate selection of reaction partners, in situ generated imines and ene-carbamates are mechanistically partitioned to yield opposing functionalized products. Formal α-functionalization to give protected α-arylamines is achieved upon enantioselective Friedel–Crafts reaction with arene nucleophiles, whereas formal β-functionalization is achieved upon reaction with diarylimine electrophiles in an enantioselective Povarov-[4+2] cycloaddition.

2,3-DISUBSTITUTED 1 -ACYL-4-AMINO-1,2,3,4-TETRAHYDROQUINOLINE DERIVATIVES AND THEIR USE AS BROMODOMAIN INHIBITORS

The present invention relates to novel compounds of formula (I), wherein R1 is C1-4alkyl; R2 is C1-4alkyl, C3-7cycloalkyl, -CH2CF3, -CH2OCH3 or heterocyclyl; R3 is C1-4alkyl, -CH2F, -CH2OH or -CH2O(O)CH3; R4 when present is as defined in claim 1; R5 when present is H, halo, hydroxy or C1-6alkoxy; A is -NH-, -O-, -S-, -SO-, -SO2-, -N(C1-4alkyl)- or -NC(O)(CH3)-; V is phenyl, heteroaromatic or pyridone any of which may be optionally substituted by 1, 2 or 3 substituents; W is CH or N; X is C or N; Y is C or N; and Z is CH or N; subject to the proviso that no more than 2 of W, X, Y and Z are N, pharmaceutical compositions containing such compounds and to their use as bromodomain inhibitors.

Syntheses of hydroxamic acid-containing bicyclic β-lactams via palladium-catalyzed oxidative amidation of alkenes

Palladium-catalyzed oxidative amidation has been used to synthesize hydroxamic acid-containing bicyclic β-lactam cores. Oxidative cleavage of the pendant alkene provides access to the carboxylic acid in one step.

Scope and limitations of ruthenium-catalyzed metathesis of simple polymer-bound alkenes

Synthetic procedures for the preparation of two types of functional resin are described, both based on 2% cross-linked polystyrene with a high density (>60%) of side-chains and terminated by a primary alcohol. In the first case the C11 side-cha

A new route to 7-substituted derivatives of N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidin-5-yl) -ethyl]benzoyl}-L-glutamic acid [ALIMTA (LY231514, MTA)]

Alkylation of various primary amines with crotyl bromide, followed by DMAP-promoted acylation with methyl malonyl chloride to 4 and then manganic triacetate dihydrate/cupric acetate induced radical cyclization, gave 1-substituted-4-vinyl-3-carbomethoxy-2-pyrrolidinones (5). Thiation to the thiolactams 6 and guanidine cyclization then gave a series of 2-amino-3,4-dihydro-4-oxo-5-vinyl-7-substituted pyrrolo[2,3-d]pyrimidines (7). Palladium-catalyzed C-C coupling with diethyl 4-iodobenzoylglutamate led in one step via an unexpected redox reaction to the diethyl esters 9 of a series of 7-substituted derivatives of ALIMTA (LY231514, MTA), from which the target analogues 10 were readily prepared by saponification. Attempted deprotection at position 7 was successful in only one case (9d, R = CH2C6H3(OMe)2 (-3′,4′), which resulted in a known pentultimate precursor (9, R = H) of ALIMTA. The 7-substituted derivatives 10 proved to be inactive in vitro as inhibitors of cell division.

Aza--Wittig Sigmatropic Rearrangement of Crotyl Amines

The first example of an acyclic aza--Wittig sigmatropic rearrangement is presented, and its application to the synthesis of unnatural amino acids is described.