tert-butyl (4S,5R)-5-{3-[4-(dimethylamino)phenyl]-2-oxo-1,3,4-oxadiazolin-5-yl}-2,2-dimethyl-4-(methylethyl)-1,3-oxazolidine-3-carboxylate

Base Information

Chemical Name:tert-butyl (4S,5R)-5-{3-[4-(dimethylamino)phenyl]-2-oxo-1,3,4-oxadiazolin-5-yl}-2,2-dimethyl-4-(methylethyl)-1,3-oxazolidine-3-carboxylate
CAS No.:342897-31-8
Molecular Formula:C₂₃H₃₄N₄O₅
Molecular Weight:446.547
Hs Code.:

Synonyms:tert-butyl (4S,5R)-5-{3-[4-(dimethylamino)phenyl]-2-oxo-1,3,4-oxadiazolin-5-yl}-2,2-dimethyl-4-(methylethyl)-1,3-oxazolidine-3-carboxylate

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Chemical Property of tert-butyl (4S,5R)-5-{3-[4-(dimethylamino)phenyl]-2-oxo-1,3,4-oxadiazolin-5-yl}-2,2-dimethyl-4-(methylethyl)-1,3-oxazolidine-3-carboxylate

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Technology Process of tert-butyl (4S,5R)-5-{3-[4-(dimethylamino)phenyl]-2-oxo-1,3,4-oxadiazolin-5-yl}-2,2-dimethyl-4-(methylethyl)-1,3-oxazolidine-3-carboxylate

There total 1 articles about tert-butyl (4S,5R)-5-{3-[4-(dimethylamino)phenyl]-2-oxo-1,3,4-oxadiazolin-5-yl}-2,2-dimethyl-4-(methylethyl)-1,3-oxazolidine-3-carboxylate 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: 63.0%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 342897-30-7
tert-butyl (4S,5R)-5-[3-(4-aminophenyl)-2-oxo-1,3,4-oxadiazolin-5-yl]-2,2-dimethyl-4-(methylethyl)-1,3-oxazolidine-3-carboxylate

: 342897-31-8
tert-butyl (4S,5R)-5-{3-[4-(dimethylamino)phenyl]-2-oxo-1,3,4-oxadiazolin-5-yl}-2,2-dimethyl-4-(methylethyl)-1,3-oxazolidine-3-carboxylate

Guidance literature:: formaldehyd; tert-butyl (4S,5R)-5-[3-(4-aminophenyl)-2-oxo-1,3,4-oxadiazolin-5-yl]-2,2-dimethyl-4-(methylethyl)-1,3-oxazolidine-3-carboxylate; With sodium cyanoborohydride; In water; acetonitrile; at 20 ℃; for 0.5h;

With acetic acid; In water; acetonitrile; for 1h; pH=4 - 5;
DOI:10.1016/S0968-0896(01)00007-4

Reference yield:

: 342897-31-8
tert-butyl (4S,5R)-5-{3-[4-(dimethylamino)phenyl]-2-oxo-1,3,4-oxadiazolin-5-yl}-2,2-dimethyl-4-(methylethyl)-1,3-oxazolidine-3-carboxylate

: 342897-32-9
{(S)-1-[(S)-2-((S)-1-{(R)-[4-(4-Dimethylamino-phenyl)-5-oxo-4,5-dihydro-[1,3,4]oxadiazol-2-yl]-hydroxy-methyl}-2-methyl-propylcarbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: ethanol / 80 °C

2: N-hydroxybenzotriazole hydrate; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl; N-methylmorpholine / dimethylformamide / 7 h / 20 °C

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In ethanol; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(01)00007-4

Reference yield:

: 342897-31-8
tert-butyl (4S,5R)-5-{3-[4-(dimethylamino)phenyl]-2-oxo-1,3,4-oxadiazolin-5-yl}-2,2-dimethyl-4-(methylethyl)-1,3-oxazolidine-3-carboxylate

: [(S)-1-((S)-2-{(S)-1-[4-(4-Dimethylamino-phenyl)-5-oxo-4,5-dihydro-[1,3,4]oxadiazole-2-carbonyl]-2-methyl-propylcarbamoyl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: ethanol / 80 °C

2: N-hydroxybenzotriazole hydrate; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl; N-methylmorpholine / dimethylformamide / 7 h / 20 °C

3: oxalyl chloride; dimethyl sulfoxide; N-methylmorpholine / CH₂Cl₂ / 2.5 h / -70 - -20 °C

With 4-methyl-morpholine; oxalyl dichloride; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In ethanol; dichloromethane; N,N-dimethyl-formamide; 3: Swern oxidation;
DOI:10.1016/S0968-0896(01)00007-4