4-[4-benzyloxycarbonylamino-2,2-difluoro-3-(imidazole-1-carbothioyloxy)-butyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

Chemical Name:4-[4-benzyloxycarbonylamino-2,2-difluoro-3-(imidazole-1-carbothioyloxy)-butyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
CAS No.:650604-97-0
Molecular Formula:C₂₆H₃₄F₂N₄O₆S
Molecular Weight:568.642
Hs Code.:

4-[4-benzyloxycarbonylamino-2,2-difluoro-3-(imidazole-1-carbothioyloxy)-butyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid <i>tert</i>-butyl ester

Synonyms:4-[4-benzyloxycarbonylamino-2,2-difluoro-3-(imidazole-1-carbothioyloxy)-butyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Chemical Property of 4-[4-benzyloxycarbonylamino-2,2-difluoro-3-(imidazole-1-carbothioyloxy)-butyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Technology Process of 4-[4-benzyloxycarbonylamino-2,2-difluoro-3-(imidazole-1-carbothioyloxy)-butyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 7 articles about 4-[4-benzyloxycarbonylamino-2,2-difluoro-3-(imidazole-1-carbothioyloxy)-butyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl 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: 81.0%

: 6160-65-2
1,1'-Thiocarbonyldiimidazole

: 650604-87-8
tert-butyl (4S)-(4-{[(benzyloxy)carbonyl]amino}-2,2-difluoro-3-hydroxybutyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

: 650604-97-0
4-[4-benzyloxycarbonylamino-2,2-difluoro-3-(imidazole-1-carbothioyloxy)-butyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: With dmap; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1039/b307563j

Reference yield:

: 153334-98-6
tert-butyl (4S)-4-(3-ethoxy-2,2-difluoro-3-oxopropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

: 650604-97-0
4-[4-benzyloxycarbonylamino-2,2-difluoro-3-(imidazole-1-carbothioyloxy)-butyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / DIBAL-H / toluene / 0.5 h / -65 °C

2: 80 percent / K₂CO₃ / tetrahydrofuran / 20 h / 20 °C

3: 91 percent / H₂ / Pd(OH)2/C / ethanol; acetic acid / 3 h / 20 °C / 3102.97 Torr

4: 78 percent / aq. NaHCO₃ / acetone / 18 h / 0 - 20 °C

5: 81 percent / DMAP / CH₂Cl₂ / 1 h / 20 °C

With dmap; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; acetic acid; acetone; toluene; 2: Henry reaction;
DOI:10.1039/b307563j

Reference yield:

: 650604-86-7
tert-butyl (4S)-4-(2,2-difluoro-3-hydroxy-4-nitrobutyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

: 650604-97-0
4-[4-benzyloxycarbonylamino-2,2-difluoro-3-(imidazole-1-carbothioyloxy)-butyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / H₂ / Pd(OH)2/C / ethanol; acetic acid / 3 h / 20 °C / 3102.97 Torr

2: 78 percent / aq. NaHCO₃ / acetone / 18 h / 0 - 20 °C

3: 81 percent / DMAP / CH₂Cl₂ / 1 h / 20 °C

With dmap; hydrogen; sodium hydrogencarbonate; palladium dihydroxide; In ethanol; dichloromethane; acetic acid; acetone;
DOI:10.1039/b307563j