(1R,2S)-methyl 1-amino-2-vinylcyclopropanecarboxylate 4-methylbenzenesulfonate

Base Information

• Chemical Name: (1R,2S)-methyl 1-amino-2-vinylcyclopropanecarboxylate 4-methylbenzenesulfonate
• CAS No.: 862273-27-6
• Molecular Formula: C₇H₈O₃S*C₇H₁₁NO₂
• Molecular Weight: 313.375
• European Community (EC) Number: 617-820-5
• DSSTox Substance ID: DTXSID901006652
• Mol file: 862273-27-6.mol

Synonyms:862273-27-6;(1R,2S)-methyl 1-amino-2-vinylcyclopropanecarboxylate 4-methylbenzenesulfonate;methyl (1R,2S)-1-amino-2-ethenylcyclopropane-1-carboxylate;4-methylbenzenesulfonic acid;(1R,2S)-methyl 1-amino-2-vinylcyclopropanecarboxylate tosylate;MFCD11616272;SCHEMBL610533;IUHJYIOSAPJUMG-HCSZTWNASA-N;DTXSID901006652;(1R,2S)-Methyl1-amino-2-vinylcyclopropanecarboxylate4-methylbenzenesulfonate;AKOS005145910;AKOS015850950;AC-27656;AS-37962;A841582;F0001-2151;(1R,2S)-methyl 1-amino-2-vinylcyclopropanecarboxylate tosylate salt;(1R,2S)-1-Amino-2-vinyl-cyclopropanecarboxylic acid methyl ester p-toluenesulfonate;1R,2S-Methyl 1-amino-2-vinylcyclopropanecarboxylic acid methyl ester Tosylate salt;4-Methylbenzene-1-sulfonic acid--methyl 1-amino-2-ethenylcyclopropane-1-carboxylate (1/1);methyl (1r,2s)-1-amino-2-vinylcyclopropane-1-carboxylate 4-methylbenzenesulfonate

Chemical Property of (1R,2S)-methyl 1-amino-2-vinylcyclopropanecarboxylate 4-methylbenzenesulfonate

Chemical Property:

• PSA: 65.58000
• LogP: 1.97990
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 313.09839388
• Heavy Atom Count: 21
• Complexity: 385

Purity/Quality:

97% ^*data from raw suppliers

(1R,2S)-Methyl1-amino-2-vinylcyclopropanecarboxylate4-methylbenzenesulfonate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)O.COC(=O)C1(CC1C=C)N
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)O.COC(=O)[C@]1(C[C@H]1C=C)N
• Uses: (1R,2S)-Methyl 1-amino-2-vinylcyclopropanecarboxylate 4-methylbenzenesulfonate is used in the asymmetric preparation of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid.

Technology Process of (1R,2S)-methyl 1-amino-2-vinylcyclopropanecarboxylate 4-methylbenzenesulfonate

There total 9 articles about (1R,2S)-methyl 1-amino-2-vinylcyclopropanecarboxylate 4-methylbenzenesulfonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 58.0%

(1R,2R)-methyl 1-t-butoxycarbonylamino-2-vinylcyclopropane carboxylate (1201943-62-5,915317-20-3) + toluene-4-sulfonic acid (104-15-4) → (1R,2R)-methyl 1-amino-2-vinylcyclopropane carboxylate tosylate salt (862273-27-6)

Guidance literature:

With water; In ethyl acetate; at 50 ℃; for 2h;

DOI:10.1021/jo061587o

Reference yield:

toluene-4-sulfonic acid (104-15-4) + (1R,2S)-1-tert-butoxycarbonylamino-2-vinyl-cyclopropanecarboxylic acid methyl ester (159622-09-0,1201943-62-5,915317-20-3) → (1R,2S)-1-amino-2-vinylcyclopropane carboxylic acid methyl ester tosylate salt (862273-27-6)

Guidance literature:

In methanol; at 40 ℃; for 2h;

DOI:10.1021/jo050468q

Reference yield:

(1S,2R)-1-{[1-Phenyl-meth-(E)-ylidene]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester → (1R,2S)-1-amino-2-vinylcyclopropane carboxylic acid methyl ester tosylate salt (862273-27-6)

Guidance literature:

Multi-step reaction with 5 steps

1: aq. HCl / toluene; various solvent(s) / 20 h / 20 °C

2: various solvent(s); toluene / 17.5 h / 20 °C

3: 95 percent / NaOMe / 2 h / Heating

4: Alcalase 2.4L(R); Na₂HPO₄*2H₂O; KCl / NaOH / acetone; H₂O / 70 h / 39 - 41 °C / pH 8.15

5: 12.1 kg / various solvent(s); methanol / 2 h / 40 °C

With hydrogenchloride; disodium hydrogenphosphate; Alcalase 2.4L(R); potassium chloride; sodium methylate; sodium hydroxide; In methanol; water; acetone; toluene;

DOI:10.1021/jo050468q

upstream raw materials:

toluene-4-sulfonic acid

(1R,2S)-1-tert-butoxycarbonylamino-2-vinyl-cyclopropanecarboxylic acid methyl ester

1-tert-butoxycarbonylamino-2-vinylcyclopropanecarboxylic acid methyl ester

rac-(1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid ethyl ester

Downstream raw materials:

(1R,2S)-1-amino-2-vinyl-cyclopropyl carboxylic acid methyl ester

(1R,2S)-2-vinyl-1-aminocyclopropanecarboxylic acid

methyl 7-phenyl-6,7-dihydro[1H]azepine-2-carboxylate