Acetic acid (2S,4S)-4-[5-((E)-2-bromo-vinyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester

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Chemical Name:Acetic acid (2S,4S)-4-[5-((E)-2-bromo-vinyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester
CAS No.:216692-83-0
Molecular Formula:C₂₀H₂₂BrN₃O₆S
Molecular Weight:512.381
Hs Code.:

Synonyms:Acetic acid (2S,4S)-4-[5-((E)-2-bromo-vinyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester

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Chemical Property of Acetic acid (2S,4S)-4-[5-((E)-2-bromo-vinyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester

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Technology Process of Acetic acid (2S,4S)-4-[5-((E)-2-bromo-vinyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester

There total 9 articles about Acetic acid (2S,4S)-4-[5-((E)-2-bromo-vinyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl 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:

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

: 216692-83-0
Acetic acid (2S,4S)-4-[5-((E)-2-bromo-vinyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 84 percent / Et₃N, DMAP / CH₂Cl₂ / 48 h / Ambient temperature

2: LiBH₄ / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 1 h

3: 100 percent / imidazole, DMAP / CH₂Cl₂ / 18 h

4: 87 percent / aq. NaN₃ / dimethylformamide / 1.) 70 deg C, 5 h, 2.) room temperature, 18 h

5: 100 percent / H₂ / Pd/C / ethanol; H₂O; ethyl acetate / 2.5 h

6: Et₃N / dioxane / 10 h / 100 °C

7: aq. HCl / 13.5 h / 90 °C

8: 82 percent / Et₃N, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

9: 1.) Br₂, AIBN, 2.) Et₃N / 1.) CHCl₃, reflux, 20 min, 2.) 90 min

With 1H-imidazole; hydrogenchloride; dmap; lithium borohydride; sodium azide; 2,2'-azobis(isobutyronitrile); hydrogen; bromine; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(98)00821-7

Reference yield:

: 118329-82-1
(2S,4R)-2-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine

: 216692-83-0
Acetic acid (2S,4S)-4-[5-((E)-2-bromo-vinyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / imidazole, DMAP / CH₂Cl₂ / 18 h

2: 87 percent / aq. NaN₃ / dimethylformamide / 1.) 70 deg C, 5 h, 2.) room temperature, 18 h

3: 100 percent / H₂ / Pd/C / ethanol; H₂O; ethyl acetate / 2.5 h

4: Et₃N / dioxane / 10 h / 100 °C

5: aq. HCl / 13.5 h / 90 °C

6: 82 percent / Et₃N, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

7: 1.) Br₂, AIBN, 2.) Et₃N / 1.) CHCl₃, reflux, 20 min, 2.) 90 min

With 1H-imidazole; hydrogenchloride; dmap; sodium azide; 2,2'-azobis(isobutyronitrile); hydrogen; bromine; triethylamine; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(98)00821-7

Reference yield:

: 16257-73-1
N,O-ditosyl-trans-4-hydroxy-L-proline methyl ester

: 216692-83-0
Acetic acid (2S,4S)-4-[5-((E)-2-bromo-vinyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: LiBH₄ / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 1 h

2: 100 percent / imidazole, DMAP / CH₂Cl₂ / 18 h

3: 87 percent / aq. NaN₃ / dimethylformamide / 1.) 70 deg C, 5 h, 2.) room temperature, 18 h

4: 100 percent / H₂ / Pd/C / ethanol; H₂O; ethyl acetate / 2.5 h

5: Et₃N / dioxane / 10 h / 100 °C

6: aq. HCl / 13.5 h / 90 °C

7: 82 percent / Et₃N, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

8: 1.) Br₂, AIBN, 2.) Et₃N / 1.) CHCl₃, reflux, 20 min, 2.) 90 min

With 1H-imidazole; hydrogenchloride; dmap; lithium borohydride; sodium azide; 2,2'-azobis(isobutyronitrile); hydrogen; bromine; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(98)00821-7