2-(Chloro-phenylsulfanyl-methyl)-2-[(2-isopropyl-oxazole-4-carbonyl)-amino]-malonic acid dimethyl ester

Base Information

• Chemical Name: 2-(Chloro-phenylsulfanyl-methyl)-2-[(2-isopropyl-oxazole-4-carbonyl)-amino]-malonic acid dimethyl ester
• CAS No.: 153180-36-0
• Molecular Formula: C₁₉H₂₁ClN₂O₆S
• Molecular Weight: 440.905
• Mol file: 153180-36-0.mol

Synonyms:2-(Chloro-phenylsulfanyl-methyl)-2-[(2-isopropyl-oxazole-4-carbonyl)-amino]-malonic acid dimethyl ester

Chemical Property of 2-(Chloro-phenylsulfanyl-methyl)-2-[(2-isopropyl-oxazole-4-carbonyl)-amino]-malonic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(Chloro-phenylsulfanyl-methyl)-2-[(2-isopropyl-oxazole-4-carbonyl)-amino]-malonic acid dimethyl ester

There total 12 articles about 2-(Chloro-phenylsulfanyl-methyl)-2-[(2-isopropyl-oxazole-4-carbonyl)-amino]-malonic acid dimethyl ester 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:

Diethyl <(isobutyryl)amino>malonate (153180-28-0) → 2-(Chloro-phenylsulfanyl-methyl)-2-[(2-isopropyl-oxazole-4-carbonyl)-amino]-malonic acid dimethyl ester (153180-36-0)

Guidance literature:

Multi-step reaction with 8 steps

1: methanol

2: NaOMe / TBAB / dimethylformamide / Ambient temperature

3: 1.) NCS, 2.) EtN(i-Pr)2 / 1.) DMF, r.t., 20 min, 2.) 16 h

4: K₂CO₃ / methanol / 1 h / Heating

5: NaOH / methanol / Ambient temperature

6: Et₃N / tetrahydrofuran / 3 h / Ambient temperature

7: Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

8: 1.) NCS, 2.) EtN(i-Pr)2 / 1.) DMF, r.t., 2 h, 2.) 16 h

With dmap; sodium hydroxide; N-chloro-succinimide; sodium methylate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; tetrabutylammomium bromide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00073a040

Reference yield:

2-Isobutyrylamino-malonic acid dimethyl ester → 2-(Chloro-phenylsulfanyl-methyl)-2-[(2-isopropyl-oxazole-4-carbonyl)-amino]-malonic acid dimethyl ester (153180-36-0)

Guidance literature:

Multi-step reaction with 7 steps

1: NaOMe / TBAB / dimethylformamide / Ambient temperature

2: 1.) NCS, 2.) EtN(i-Pr)2 / 1.) DMF, r.t., 20 min, 2.) 16 h

3: K₂CO₃ / methanol / 1 h / Heating

4: NaOH / methanol / Ambient temperature

5: Et₃N / tetrahydrofuran / 3 h / Ambient temperature

6: Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

7: 1.) NCS, 2.) EtN(i-Pr)2 / 1.) DMF, r.t., 2 h, 2.) 16 h

With dmap; sodium hydroxide; N-chloro-succinimide; sodium methylate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; tetrabutylammomium bromide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00073a040

Reference yield:

phenylthiomethyl chloride (7205-91-6) → 2-(Chloro-phenylsulfanyl-methyl)-2-[(2-isopropyl-oxazole-4-carbonyl)-amino]-malonic acid dimethyl ester (153180-36-0)

Guidance literature:

Multi-step reaction with 4 steps

1: NaOMe / TBAB / dimethylformamide / 16 h / Ambient temperature

2: 98 percent / TFA / CH₂Cl₂ / Ambient temperature

3: Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

4: 1.) NCS, 2.) EtN(i-Pr)2 / 1.) DMF, r.t., 2 h, 2.) 16 h

With dmap; N-chloro-succinimide; sodium methylate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; tetrabutylammomium bromide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00073a040

upstream raw materials:

N-<1',1'-Bis(methoxycarbonyl)-2'-(phenylthio)ethyl>-2-isopropyloxazole-4-carboxamide

phenylthiomethyl chloride

Diethyl <(isobutyryl)amino>malonate

dimethyl 2-(tert-butoxycarbonylamino)malonate

Downstream raw materials:

N-<1'',1''-Bis(methoxycarbonyl)-2''-(phenylthio)ethyl>-2'-isopropyl-<2,4'-bioxazole>-4-carboxamide

Refernces