3-Oxazolidinecarboxylic acid, 4-[[[1-[6-(dimethoxymethyl)-3-[4-(ethoxycarbonyl)-2-thiazolyl]-2-pyridinyl] ethenyl]amino]carbonyl]-2,2-dimethyl-, phenylmethyl ester, (4S)-

Base Information

• Chemical Name: 3-Oxazolidinecarboxylic acid, 4-[[[1-[6-(dimethoxymethyl)-3-[4-(ethoxycarbonyl)-2-thiazolyl]-2-pyridinyl] ethenyl]amino]carbonyl]-2,2-dimethyl-, phenylmethyl ester, (4S)-
• CAS No.: 666215-55-0
• Molecular Formula: C₃₀H₃₄N₄O₈S
• Molecular Weight: 610.688

Synonyms:

Chemical Property of 3-Oxazolidinecarboxylic acid, 4-[[[1-[6-(dimethoxymethyl)-3-[4-(ethoxycarbonyl)-2-thiazolyl]-2-pyridinyl] ethenyl]amino]carbonyl]-2,2-dimethyl-, phenylmethyl ester, (4S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 3-Oxazolidinecarboxylic acid, 4-[[[1-[6-(dimethoxymethyl)-3-[4-(ethoxycarbonyl)-2-thiazolyl]-2-pyridinyl] ethenyl]amino]carbonyl]-2,2-dimethyl-, phenylmethyl ester, (4S)-

There total 8 articles about 3-Oxazolidinecarboxylic acid, 4-[[[1-[6-(dimethoxymethyl)-3-[4-(ethoxycarbonyl)-2-thiazolyl]-2-pyridinyl] ethenyl]amino]carbonyl]-2,2-dimethyl-, phenylmethyl ester, (4S)- 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: 64.0%

methanesulfonyl chloride (124-63-0) + (S)-4-{1-[6-Dimethoxymethyl-3-(4-ethoxycarbonyl-thiazol-2-yl)-pyridin-2-yl]-2-hydroxy-ethylcarbamoyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (666215-54-9) → (S)-4-{1-[6-Dimethoxymethyl-3-(4-ethoxycarbonyl-thiazol-2-yl)-pyridin-2-yl]-vinylcarbamoyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (666215-55-0)

Guidance literature:

methanesulfonyl chloride; (S)-4-{1-[6-Dimethoxymethyl-3-(4-ethoxycarbonyl-thiazol-2-yl)-pyridin-2-yl]-2-hydroxy-ethylcarbamoyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester; With triethylamine;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In chloroform;

DOI:10.3987/COM-03-S27

Reference yield:

2-(6-Dimethoxymethyl-2-trifluoromethanesulfonyloxy-pyridin-3-yl)-thiazole-4-carboxylic acid ethyl ester (214040-92-3) → (S)-4-{1-[6-Dimethoxymethyl-3-(4-ethoxycarbonyl-thiazol-2-yl)-pyridin-2-yl]-vinylcarbamoyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (666215-55-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 96 percent / LiCl; Pd(PPh₃)4 / tetrahydrofuran

2.1: 90 percent / OsO₄; N-methylmorpholine N-oxide / CHCl₃

3.1: Et₃N

4.1: Et₃N

5.1: NaN₃ / dimethylformamide

6.1: H₂ / 10 percent Pd-C / methanol

6.2: 89 percent / diphenyl phosphorazidate; Et₃N

7.1: 87 percent / tetrabutylammonium fluoride / tetrahydrofuran

8.1: Et₃N

8.2: 64 percent / DBU / CHCl₃

With osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; tetrabutyl ammonium fluoride; hydrogen; 4-methylmorpholine N-oxide; triethylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide;

DOI:10.3987/COM-03-S27

Reference yield:

2-(6-dimethoxymethyl-2-vinyl-pyridin-3-yl)-thiazole-4-carboxylic acid ethyl ester (666215-49-2) → (S)-4-{1-[6-Dimethoxymethyl-3-(4-ethoxycarbonyl-thiazol-2-yl)-pyridin-2-yl]-vinylcarbamoyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (666215-55-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 90 percent / OsO₄; N-methylmorpholine N-oxide / CHCl₃

2.1: Et₃N

3.1: Et₃N

4.1: NaN₃ / dimethylformamide

5.1: H₂ / 10 percent Pd-C / methanol

5.2: 89 percent / diphenyl phosphorazidate; Et₃N

6.1: 87 percent / tetrabutylammonium fluoride / tetrahydrofuran

7.1: Et₃N

7.2: 64 percent / DBU / CHCl₃

With osmium(VIII) oxide; sodium azide; tetrabutyl ammonium fluoride; hydrogen; 4-methylmorpholine N-oxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide;

DOI:10.3987/COM-03-S27

upstream raw materials:

methanesulfonyl chloride

(S)-4-{1-[6-Dimethoxymethyl-3-(4-ethoxycarbonyl-thiazol-2-yl)-pyridin-2-yl]-2-hydroxy-ethylcarbamoyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

2-(6-Dimethoxymethyl-2-trifluoromethanesulfonyloxy-pyridin-3-yl)-thiazole-4-carboxylic acid ethyl ester

2-(6-dimethoxymethyl-2-vinyl-pyridin-3-yl)-thiazole-4-carboxylic acid ethyl ester

Downstream raw materials:

(S)-4-{2-Bromo-1-[6-dimethoxymethyl-3-(4-ethoxycarbonyl-thiazol-2-yl)-pyridin-2-yl]-1-methoxy-ethylcarbamoyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

2-(2-{2-[1-benzyloxycarbonylamino-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-oxazol-4-yl}-6-dimethoxymethyl-pyridin-3-yl)-thiazole-4-carboxylic acid ethyl ester

2-(2-{2-[1-amino-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-oxazol-4-yl}-6-dimethoxymethyl-pyridin-3-yl)-thiazole-4-carboxylic acid ethyl ester

(S)-4-[6-Dimethoxymethyl-3-(4-ethoxycarbonyl-thiazol-2-yl)-pyridin-2-yl]-2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid benzyl ester

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