Hydrazinecarboxylic acid, 2-(2-methoxy-1-methyl-2-oxoethyl)-, 1,1-dimethylethyl ester, (R)-

Base Information

• Chemical Name: Hydrazinecarboxylic acid, 2-(2-methoxy-1-methyl-2-oxoethyl)-, 1,1-dimethylethyl ester, (R)-
• CAS No.: 130608-07-0
• Molecular Formula: C₉H₁₈N₂O₄
• Molecular Weight: 218.253
• DSSTox Substance ID: DTXSID301121062
• Mol file: 130608-07-0.mol

Synonyms:DTXSID301121062;Hydrazinecarboxylic acid, 2-(2-methoxy-1-methyl-2-oxoethyl)-, 1,1-dimethylethyl ester, (R)-;130608-07-0

Chemical Property of Hydrazinecarboxylic acid, 2-(2-methoxy-1-methyl-2-oxoethyl)-, 1,1-dimethylethyl ester, (R)-

Chemical Property:

• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 218.12665706
• Heavy Atom Count: 15
• Complexity: 235

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C(=O)OC)NNC(=O)OC(C)(C)C
• Isomeric SMILES: C[C@H](C(=O)OC)NNC(=O)OC(C)(C)C

Technology Process of Hydrazinecarboxylic acid, 2-(2-methoxy-1-methyl-2-oxoethyl)-, 1,1-dimethylethyl ester, (R)-

There total 14 articles about Hydrazinecarboxylic acid, 2-(2-methoxy-1-methyl-2-oxoethyl)-, 1,1-dimethylethyl ester, (R)- 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: 88.0%

(R)-Methyl lactate (17392-83-5,2155-30-8) + t-butoxycarbonylhydrazine (870-46-2) → tert-butyl 2-((S)-2-methoxy-1-methyl-2-oxoethyl)hydrazinecarboxylate (130518-03-5,130608-07-0,151004-11-4)

Guidance literature:

(R)-Methyl lactate; With 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

t-butoxycarbonylhydrazine; In dichloromethane; at 0 ℃; for 6.5h; Inert atmosphere;

DOI:10.1016/j.tetlet.2017.02.026

Reference yield: 82.0%

tert-butyl N-tosyloxycarbamate (105838-14-0) + L-alanine methyl ester hydrochloride (2491-20-5) → tert-butyl 2-((S)-2-methoxy-1-methyl-2-oxoethyl)hydrazinecarboxylate (130518-03-5,130608-07-0,151004-11-4)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 20 - 25 ℃; for 3h;

DOI:10.1016/j.tetlet.2012.02.075

Reference yield: 74.0%

L-alanine methyl ester hydrochloride (2491-20-5) + oxaziridine-2,3,3-tricarboxylic acid 2-tert-butyl ester 3,3-diethyl ester (462100-44-3) → tert-butyl 2-((S)-2-methoxy-1-methyl-2-oxoethyl)hydrazinecarboxylate (130518-03-5,130608-07-0,151004-11-4)

Guidance literature:

L-alanine methyl ester hydrochloride; With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃; for 0.166667h; Inert atmosphere;

oxaziridine-2,3,3-tricarboxylic acid 2-tert-butyl ester 3,3-diethyl ester; In tetrahydrofuran; water; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.joc.6b02718

upstream raw materials:

t-butoxycarbonylhydrazine

(S)-(-)-2-(4'-Nitrophenylsulfonyloxy)-propionsaeure-methylester

L-Alanine methyl ester

N-tert-butyloxycarbonyl-3-(4-cyanophenyl)oxaziridine

Refernces

• 1、 -. "SULFONAMIDE COMPOUNDS HAVING TNAP INHIBITORY ACTIVITY". Page/Page column 112; 153; 154; 155. . Retrieved 2018/07/29.
• 2、 Mehawed Abdellatif, Mohamed,Acherar, Samir. "Low-cost and multi-gram scale synthesis of chiral Nβ-Boc protected α-Nα-hydrazino diesters". supporting information. p. 1216 - 1218. Retrieved 2017/03/02.