259221-77-7

Basic information

• Product Name: CYCLOPROPANECARBOXYLIC ACID, 1-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-2-ETHENYL-, (1S,2S)-
• Synonyms: CYCLOPROPANECARBOXYLIC ACID, 1-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-2-ETHENYL-, (1S,2S)-;(1S,2S)-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylic acid;(1R,2S)-1-(tert-Butoxycarbonylamino)-2-vinylcyclopropanecarboxylic acid
• CAS NO: 259221-77-7
• Molecular Formula: C11H17NO4
• Molecular Weight: 227.258
• Mol File: 259221-77-7.mol
• Article Data: 46

Chemical Properties

• Boiling Point: 361 °C at 760 mmHg
• Flash Point: 172.1 °C
• Appearance: /
• Density: 1.17 g/cm³
• Refractive Index: 1.508
• CAS DataBase Reference: CYCLOPROPANECARBOXYLIC ACID, 1-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-2-ETHENYL-, (1S,2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLOPROPANECARBOXYLIC ACID, 1-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-2-ETHENYL-, (1S,2S)-(259221-77-7)
• EPA Substance Registry System: CYCLOPROPANECARBOXYLIC ACID, 1-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-2-ETHENYL-, (1S,2S)-(259221-77-7)

Safety Data

• Hazardous Substances Data: 259221-77-7(Hazardous Substances Data)

Usage

General Description

CYCLOPROPANECARBOXYLIC ACID, 1-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-2-ETHENYL-, (1S,2S)- is a chemical compound with a molecular formula C13H21NO3. It is also known as Cyclopropylglycine and is a derivative of glycine. CYCLOPROPANECARBOXYLIC ACID, 1-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-2-ETHENYL-, (1S,2S)- is a white crystalline solid and is used in the pharmaceutical industry as a building block for the synthesis of various drugs and pharmaceuticals. It is also used as a chiral auxiliary in asymmetric synthesis. The compound has potential biological activity and is being studied for its potential applications in medicinal chemistry and drug development.

InChI:InChI=1/C11H17NO4/c1-5-7-6-11(7,8(13)14)12-9(15)16-10(2,3)4/h5,7H,1,6H2,2-4H3,(H,12,15)(H,13,14)/t7-,11?/m1/s1

Upstream product

• 787548-29-2 (1R,2S)/(1S,2R) 1-amino-2-vinylcyclopropane carboxylic acid ethyl ester 
• 1393095-18-5 (E)-ethyl 1-(benzylideneamino)-2-vinylcyclopropanecarboxylate 
• 681807-59-0 (1R,2S)-ethyl 1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 862273-27-6 1-amino-2-ethenylcyclopropylcarboxylic acid tosylate 
• 1023795-84-7 C₂₁H₂₁NO₂ 
• 213316-32-6 rac-(1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid ethyl ester 
• 924307-75-5 (1S,2R)-ethyl 2-vinyl-1-(tert-butoxycarbonylamino)cyclopropanecarboxylate 
• 213316-49-5 (1RS,2SR)-ethyl 2-vinyl-1-(tert-butoxycarbonylamino)cyclopropanecarboxylate 
• 1201943-62-5 1-tert-butoxycarbonylamino-2-vinylcyclopropanecarboxylic acid methyl ester 
• 159700-58-0 (1R,2S)-2-vinyl-1-aminocyclopropanecarboxylic acid 
• 1221174-65-7 (1S,2S)-2-vinyl-1-carbamoylcyclopropanecarboxylic acid (S)-N-benzyl-1-phenylethylamine salt 
• 158665-23-7 (Z)-1-carbamoyl-2-ethenylcyclopropanecarboxylic acid 
• 1221174-69-1 sodium (1S,2S)-2-vinyl-1-carbamoylcyclopropanecarboxylate 

Downstream Products

• 630421-48-6 tert-butyl ((1R,2S)-1-{[(cyclopropylsulfonyl)amino]carbonyl}-2-vinylcyclopropyl)carbamate 
• 853269-57-5 tert-butyl [(1R,2S)-2-ethenyl-1-{[(1-methylcyclopropyl)sulfonyl]carbamoyl}cyclopropyl]carbamate 
• 159622-09-0 (1R,2S)-1-tert-butoxycarbonylamino-2-vinyl-cyclopropanecarboxylic acid methyl ester 
• 923591-34-8 tert-butyl ((1R,2R)-1-{[(cyclopropylsulfonyl)amino]carbonyl}-2-ethylcyclopropyl)carbamate 
• 1028252-79-0 C₃₁H₃₁F₃N₄O₇S 
• 1028252-78-9 C₃₆H₃₉F₃N₄O₉S 
• 1028329-00-1 C₃₇H₄₂F₃N₅O₈S 
• 1028252-80-3 C₄₂H₅₀F₃N₅O₁₀S 
• 954271-75-1 [(1R,2S)-1-(2-amino-benzenesulfonylaminocarbonyl)-2-vinyl-cyclopropyl]-carbamic acid tert-butyl ester 
• 1051391-84-4 9-{2-[((1R,2S)-1-amino-2-vinyl-cyclopropanecarbonyl)-sulfamoyl]-phenylamino}-nonanoic acid methyl ester 
• 1051391-83-3 9-{2-[((1R,2S)-1-tert-butoxycarbonylamino-2-vinyl-cyclopropanecarbonyl)-sulfamoyl]-phenylamino}-nonanoic acid methyl ester 
• 1051391-38-8 8-{2-[((1R,2S)-1-tert-butoxycarbonylamino-2-vinyl-cyclopropanecarbonyl)-sulfamoyl]-phenylcarbamoyl}-octanoic acid methyl ester 
• 1051391-40-2 8-{2-[((1R,2S)-1-amino-2-vinyl-cyclopropanecarbonyl)-sulfamoyl]-phenylcarbamoyl}-octanoic acid methyl ester hydrochloride 
• 1051388-88-5 (8S,10R)-10-(7-methoxy-2-phenyl-quinolin-4-yloxy)-5-[(1R,2S)-1-carbonylamino-2-vinyl-cyclopropyl]-2,2-dioxo-2λ*6*-thia-3,6,12,22-tetraaza-tricyclo[21.4.0.0*8,12*]heptacosa-1(27),23,25-triene-4,7,13,21-tetraone 

Relevant articles and documents

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METHOD FOR SYNTHESIZING OPTICALLY ACTIVE a-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL] ACETAMIDE COMPOUND AND AMINO ACID

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Advanced asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by alkylation/cyclization of newly designed axially chiral Ni(II) complex of glycine Schiff base

Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid (vinyl-ACCA) is in extremely high demand due to the pharmaceutical importance of this tailor-made, sterically constrained α-amino acid. Here we report the development of an advanced procedure for preparation of the target amino acid via two-step SN2 and SN2′ alkylation of novel axially chiral nucleophilic glycine equivalent. Excellent yields and diastereoselectivity coupled with reliable and easy scalability render this method of immediate use for practical synthesis of (1R,2S)-vinyl-ACCA.