(-)-(3aR,6aS)-N-[(1S)-1-(4-benzoyl-6,6-dimethoxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]-4-tert-butylbenzamide

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Chemical Name:(-)-(3aR,6aS)-N-[(1S)-1-(4-benzoyl-6,6-dimethoxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]-4-tert-butylbenzamide
CAS No.:648936-13-4
Molecular Formula:C₃₂H₄₃N₃O₅
Molecular Weight:549.711
Hs Code.:

Synonyms:(-)-(3aR,6aS)-N-[(1S)-1-(4-benzoyl-6,6-dimethoxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]-4-tert-butylbenzamide

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Chemical Property of (-)-(3aR,6aS)-N-[(1S)-1-(4-benzoyl-6,6-dimethoxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]-4-tert-butylbenzamide

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Technology Process of (-)-(3aR,6aS)-N-[(1S)-1-(4-benzoyl-6,6-dimethoxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]-4-tert-butylbenzamide

There total 19 articles about (-)-(3aR,6aS)-N-[(1S)-1-(4-benzoyl-6,6-dimethoxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]-4-tert-butylbenzamide 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:

: 648936-12-3
(2S,3aR,6aS)-2-amino-1-(4-benzoyl-6,6-dimethoxyhexahydropyrrolo[3,2-b]pyrrol-1-yl)-4-methylpentan-1-one

: 98-73-7
4-(1,1-dimethylethyl)benzoic acid

: 648936-13-4
(-)-(3aR,6aS)-N-[(1S)-1-(4-benzoyl-6,6-dimethoxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]-4-tert-butylbenzamide

Guidance literature:: With 4-methyl-morpholine; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 1.83333h;
DOI:10.1016/j.bmc.2004.10.060

Reference yield:

: 648936-21-4
(R)-2-(2-aminoethyl)-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester

: 648936-13-4
(-)-(3aR,6aS)-N-[(1S)-1-(4-benzoyl-6,6-dimethoxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]-4-tert-butylbenzamide

Guidance literature:: Multi-step reaction with 11 steps

1.1: sodium carbonate / dioxane; H₂O / 1 h

2.1: meta-chloroperbenzoic acid / CH₂Cl₂ / 16 h / 20 °C

3.1: hydrogen / Pd/C / ethanol / 0 - 20 °C

3.2: 61 percent / sodium carbonate / dioxane; H₂O / 1 h

4.1: HCl / dioxane / 1.08 h / 20 °C

5.1: N-methylmorpholine / dimethylformamide / 1.75 h / 20 °C

6.1: 78 percent / Dess-Martin periodinane / CH₂Cl₂ / 16 h

7.1: 77 percent / para-toluenesulfonic acid / methanol / 16 h / 65 °C

8.1: hydrogen / Pd/C / methanol / 1.42 h / 20 °C

9.1: 0.55 g / dimethylformamide / 1 h / 20 °C

10.1: hydrogen / Pd/C / methanol / 7.75 h / 20 °C

11.1: N-methylmorpholine; 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium PF₆^(1-); 1-hydroxybenzotriazole / dimethylformamide / 1.83 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; hydrogen; sodium carbonate; benzotriazol-1-ol; Dess-Martin periodane; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Schotten-Baumann reaction / 3.2: Schotten-Baumann reaction;
DOI:10.1016/j.bmc.2004.10.060

Reference yield:

: 648930-83-0
(S)-2-(2-diazoacetyl)-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester

: 648936-13-4
(-)-(3aR,6aS)-N-[(1S)-1-(4-benzoyl-6,6-dimethoxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]-4-tert-butylbenzamide

Guidance literature:: Multi-step reaction with 16 steps

1.1: 72 percent / silver trifluoroacetate; N-methylmorpholine / tetrahydrofuran / 6 h / 0 - 20 °C

2.1: 67 percent / lithium borohydride / methanol; tetrahydrofuran / 1.25 h

3.1: 3.42 g / triethylamine / CH₂Cl₂ / 1 h / 0 °C

4.1: sodium azide / dimethylformamide / 1.5 h / 60 °C

5.1: triphenylphosphine / tetrahydrofuran / 7.5 h / 45 °C

6.1: sodium carbonate / dioxane; H₂O / 1 h

7.1: meta-chloroperbenzoic acid / CH₂Cl₂ / 16 h / 20 °C

8.1: hydrogen / Pd/C / ethanol / 0 - 20 °C

8.2: 61 percent / sodium carbonate / dioxane; H₂O / 1 h

9.1: HCl / dioxane / 1.08 h / 20 °C

10.1: N-methylmorpholine / dimethylformamide / 1.75 h / 20 °C

11.1: 78 percent / Dess-Martin periodinane / CH₂Cl₂ / 16 h

12.1: 77 percent / para-toluenesulfonic acid / methanol / 16 h / 65 °C

13.1: hydrogen / Pd/C / methanol / 1.42 h / 20 °C

14.1: 0.55 g / dimethylformamide / 1 h / 20 °C

15.1: hydrogen / Pd/C / methanol / 7.75 h / 20 °C

16.1: N-methylmorpholine; 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium PF₆^(1-); 1-hydroxybenzotriazole / dimethylformamide / 1.83 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; lithium borohydride; sodium azide; hydrogen; silver trifluoroacetate; sodium carbonate; benzotriazol-1-ol; Dess-Martin periodane; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Wolff rearrangement / 6.1: Schotten-Baumann reaction / 8.2: Schotten-Baumann reaction;
DOI:10.1016/j.bmc.2004.10.060