(R)-3-methyl-2-((7aR)-7a-methyl-5-oxo-(7ar)-hexahydro-pyrrolo[2,1-b]thiazole-3t-carbonylamino)-but-3-enoic acid benzyl ester

Base Information

Chemical Name:(R)-3-methyl-2-((7aR)-7a-methyl-5-oxo-(7ar)-hexahydro-pyrrolo[2,1-b]thiazole-3t-carbonylamino)-but-3-enoic acid benzyl ester
CAS No.:67471-75-4
Molecular Formula:C₂₀H₂₄N₂O₄S
Molecular Weight:388.488
Hs Code.:

(<i>R</i>)-3-methyl-2-((7a<i>R</i>)-7a-methyl-5-oxo-(7a<i>r</i>)-hexahydro-pyrrolo[2,1-<i>b</i>]thiazole-3<i>t</i>-carbonylamino)-but-3-enoic acid benzyl ester

Synonyms:(R)-3-methyl-2-((7aR)-7a-methyl-5-oxo-(7ar)-hexahydro-pyrrolo[2,1-b]thiazole-3t-carbonylamino)-but-3-enoic acid benzyl ester

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Chemical Property of (R)-3-methyl-2-((7aR)-7a-methyl-5-oxo-(7ar)-hexahydro-pyrrolo[2,1-b]thiazole-3t-carbonylamino)-but-3-enoic acid benzyl ester

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Technology Process of (R)-3-methyl-2-((7aR)-7a-methyl-5-oxo-(7ar)-hexahydro-pyrrolo[2,1-b]thiazole-3t-carbonylamino)-but-3-enoic acid benzyl ester

There total 2 articles about (R)-3-methyl-2-((7aR)-7a-methyl-5-oxo-(7ar)-hexahydro-pyrrolo[2,1-b]thiazole-3t-carbonylamino)-but-3-enoic acid benzyl 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:

: 624-45-3
levulinic acid methyl ester

: 67471-75-4
(R)-3-methyl-2-((7aR)-7a-methyl-5-oxo-(7ar)-hexahydro-pyrrolo[2,1-b]thiazole-3t-carbonylamino)-but-3-enoic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: MeSO₃H / 4 h / 120 °C

2: DCC, 1-hydroxy-1H-<1,2,3>benzotriazole / CH₂Cl₂ / Ambient temperature

With methanesulfonic acid; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane;
DOI:10.1021/ja00482a048

Reference yield:

: 67505-13-9
(7aR)-7a-methyl-5-oxo-(7ar)-hexahydro-pyrrolo[2,1-b]thiazole-3t-carboxylic acid

: 67471-85-6
(R)-3-methyl-but-3-enoic acid benzyl ester

: 67471-75-4
(R)-3-methyl-2-((7aR)-7a-methyl-5-oxo-(7ar)-hexahydro-pyrrolo[2,1-b]thiazole-3t-carbonylamino)-but-3-enoic acid benzyl ester

Guidance literature:: With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; Ambient temperature;
DOI:10.1021/ja00482a048

Reference yield:

: 67471-75-4
(R)-3-methyl-2-((7aR)-7a-methyl-5-oxo-(7ar)-hexahydro-pyrrolo[2,1-b]thiazole-3t-carbonylamino)-but-3-enoic acid benzyl ester

: 67471-79-8
10-chloro-6β-(4-oxo-pentanoylamino)-penicillanic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: CCl₄ / 1 h / 65 °C

2: HCl / CH₂Cl₂ / 2 h / 0 °C

3: NaH / paraffin / 0.42 h / 0 °C

4: aq. tBuOCl / tetrahydrofuran / 1.5 h / -78 °C

With hydrogenchloride; tert-butylhypochlorite; sodium hydride; In tetrahydrofuran; tetrachloromethane; dichloromethane; paraffin;
DOI:10.1021/ja00482a048