[(2R,5aS,10aS)-5,10-Dioxo-2-(toluene-4-sulfonyloxy)-hexahydro-dipyrrolo[1,2-a;1',2'-d]pyrazin-5a-yl]-acetic acid tert-butyl ester

Base Information

Chemical Name:[(2R,5aS,10aS)-5,10-Dioxo-2-(toluene-4-sulfonyloxy)-hexahydro-dipyrrolo[1,2-a;1',2'-d]pyrazin-5a-yl]-acetic acid tert-butyl ester
CAS No.:195453-86-2
Molecular Formula:C₂₃H₃₀N₂O₇S
Molecular Weight:478.566
Hs Code.:

Synonyms:[(2R,5aS,10aS)-5,10-Dioxo-2-(toluene-4-sulfonyloxy)-hexahydro-dipyrrolo[1,2-a;1',2'-d]pyrazin-5a-yl]-acetic acid tert-butyl ester

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Chemical Property of [(2R,5aS,10aS)-5,10-Dioxo-2-(toluene-4-sulfonyloxy)-hexahydro-dipyrrolo[1,2-a;1',2'-d]pyrazin-5a-yl]-acetic acid tert-butyl ester

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Technology Process of [(2R,5aS,10aS)-5,10-Dioxo-2-(toluene-4-sulfonyloxy)-hexahydro-dipyrrolo[1,2-a;1',2'-d]pyrazin-5a-yl]-acetic acid tert-butyl ester

There total 7 articles about [(2R,5aS,10aS)-5,10-Dioxo-2-(toluene-4-sulfonyloxy)-hexahydro-dipyrrolo[1,2-a;1',2'-d]pyrazin-5a-yl]-acetic 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: 91.0%

: 98-59-9
p-toluenesulfonyl chloride

: 195453-76-0
((2R,5aS,10aS)-2-Hydroxy-5,10-dioxo-hexahydro-dipyrrolo[1,2-a;1',2'-d]pyrazin-5a-yl)-acetic acid tert-butyl ester

: 195453-86-2
[(2R,5aS,10aS)-5,10-Dioxo-2-(toluene-4-sulfonyloxy)-hexahydro-dipyrrolo[1,2-a;1',2'-d]pyrazin-5a-yl]-acetic acid tert-butyl ester

Guidance literature:: With pyridine; at 0 ℃; for 3h;
DOI:10.1002/hlca.19970800514

Reference yield:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 195453-86-2
[(2R,5aS,10aS)-5,10-Dioxo-2-(toluene-4-sulfonyloxy)-hexahydro-dipyrrolo[1,2-a;1',2'-d]pyrazin-5a-yl]-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 42 percent / i-Pr₂EtN, O-(1H-benzotriazol-1-yl)-N,N,N'',N''-tetramethyluronium hexafluorophosphate / CH₂Cl₂ / 4.5 h / Ambient temperature

2: 83 percent / H₂ / 10percent Pd/C / ethyl acetate / 36 h

3: 91 percent / pyridine / 3 h / 0 °C

With pyridine; hydrogen; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate;
DOI:10.1002/hlca.19970800514

Reference yield:

: 5211-23-4
N-carbobenzyloxy-L-proline methyl ester

: 195453-86-2
[(2R,5aS,10aS)-5,10-Dioxo-2-(toluene-4-sulfonyloxy)-hexahydro-dipyrrolo[1,2-a;1',2'-d]pyrazin-5a-yl]-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / LDA/THF complex / tetrahydrofuran; hexane

2: 83 percent / LiOH*H₂O / methanol; H₂O / 15 h

3: 42 percent / i-Pr₂EtN, O-(1H-benzotriazol-1-yl)-N,N,N'',N''-tetramethyluronium hexafluorophosphate / CH₂Cl₂ / 4.5 h / Ambient temperature

4: 83 percent / H₂ / 10percent Pd/C / ethyl acetate / 36 h

5: 91 percent / pyridine / 3 h / 0 °C

With tetrahydrofuran; pyridine; lithium hydroxide; hydrogen; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate;
DOI:10.1002/hlca.19970800514