3a-{3-[2-tert-butoxycarbonylamino-2-(1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-ethyl]-1H-indol-7-yl}-2-(1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,8-dicarboxylic acid di-tert-butyl ester

Base Information

• Chemical Name: 3a-{3-[2-tert-butoxycarbonylamino-2-(1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-ethyl]-1H-indol-7-yl}-2-(1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,8-dicarboxylic acid di-tert-butyl ester
• CAS No.: 370890-28-1
• Molecular Formula: C₅₇H₆₈N₆O₁₂
• Molecular Weight: 1029.2

Synonyms:3a-{3-[2-tert-butoxycarbonylamino-2-(1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-ethyl]-1H-indol-7-yl}-2-(1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,8-dicarboxylic acid di-tert-butyl ester

Chemical Property of 3a-{3-[2-tert-butoxycarbonylamino-2-(1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-ethyl]-1H-indol-7-yl}-2-(1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,8-dicarboxylic acid di-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3a-{3-[2-tert-butoxycarbonylamino-2-(1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-ethyl]-1H-indol-7-yl}-2-(1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,8-dicarboxylic acid di-tert-butyl ester

There total 20 articles about 3a-{3-[2-tert-butoxycarbonylamino-2-(1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-ethyl]-1H-indol-7-yl}-2-(1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,8-dicarboxylic acid di-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:

di-tert-butyl dicarbonate (24424-99-5) → 3a-{3-[2-tert-butoxycarbonylamino-2-(1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-ethyl]-1H-indol-7-yl}-2-(1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,8-dicarboxylic acid di-tert-butyl ester (370890-28-1)

Guidance literature:

Multi-step reaction with 19 steps

1.1: aq. Na₂CO₃ / dioxane

2.1: NaBH₄; LiCl / ethanol; tetrahydrofuran

3.1: p-TsOH / benzene

4.1: s-BuLi; TMEDA / diethyl ether / -78 °C

4.2: 73 percent / 1,2-diiodoethane / diethyl ether

5.1: DDQ; K₂CO₃ / toluene / 70 °C

6.1: (2-furyl)3P; CuI; NMP / Pd₂(dba)3*CHCl₃

7.1: DMSO / dimethylsulfoxide / 130 °C

8.1: 94 percent / Me₃Al; K₂CO₃ / CH₂Cl₂

9.1: NaH / dimethylformamide

9.2: 79 percent / dimethylformamide

10.1: 66 percent / (2-furyl)3P; PMP; DMA / Pd₂(dba)3*CHCl₃ / 90 °C

11.1: 85 percent / Bu₄NF

12.1: 95 percent / H₂ / 10 percent Pd/C / dimethylformamide / 51714.8 Torr

13.1: 1 N HCl / dioxane / 50 °C

14.1: 17 percent / 1 N NaOH; Bu₄NHSO₄ / CH₂Cl₂

15.1: LiEt₃BH / tetrahydrofuran / -78 - 0 °C

15.2: HCl / tetrahydrofuran; diethyl ether / 0 - 20 °C

16.1: KOH / methanol

17.1: SO₃*pyr; Et₃N; DMSO

18.1: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol

19.1: HATU; Et₃N / CH₂Cl₂

With 1-methyl-pyrrolidin-2-one; hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; copper(l) iodide; 2-methyl-but-2-ene; trifuran-2-yl-phosphane; pyridine-SO₃ complex; N,N,N,N,-tetramethylethylenediamine; 2-isovalerylindane-1,3-dione; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; sec.-butyllithium; tetra(n-butyl)ammonium hydrogensulfate; 2,4-dichlorophenoxyacetic acid dimethylamine; sodium hydride; lithium triethylborohydride; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium chloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene; 6.1: Stille coupling / 8.1: Weinreb aminolysis;

DOI:10.1021/ja016616l

Reference yield:

(S)-tryptophan methyl ester hydrochloride (7524-52-9,26988-71-6,5619-09-0,14907-27-8,41222-70-2,67557-19-1,109492-62-8) → 3a-{3-[2-tert-butoxycarbonylamino-2-(1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-ethyl]-1H-indol-7-yl}-2-(1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,8-dicarboxylic acid di-tert-butyl ester (370890-28-1)

Guidance literature:

Multi-step reaction with 20 steps

1.1: Et₃SiH; TFA / 50 °C

2.1: aq. Na₂CO₃ / dioxane

3.1: NaBH₄; LiCl / ethanol; tetrahydrofuran

4.1: p-TsOH / benzene

5.1: s-BuLi; TMEDA / diethyl ether / -78 °C

5.2: 73 percent / 1,2-diiodoethane / diethyl ether

6.1: DDQ; K₂CO₃ / toluene / 70 °C

7.1: (2-furyl)3P; CuI; NMP / Pd₂(dba)3*CHCl₃

8.1: DMSO / dimethylsulfoxide / 130 °C

9.1: 94 percent / Me₃Al; K₂CO₃ / CH₂Cl₂

10.1: NaH / dimethylformamide

10.2: 79 percent / dimethylformamide

11.1: 66 percent / (2-furyl)3P; PMP; DMA / Pd₂(dba)3*CHCl₃ / 90 °C

12.1: 85 percent / Bu₄NF

13.1: 95 percent / H₂ / 10 percent Pd/C / dimethylformamide / 51714.8 Torr

14.1: 1 N HCl / dioxane / 50 °C

15.1: 17 percent / 1 N NaOH; Bu₄NHSO₄ / CH₂Cl₂

16.1: LiEt₃BH / tetrahydrofuran / -78 - 0 °C

16.2: HCl / tetrahydrofuran; diethyl ether / 0 - 20 °C

17.1: KOH / methanol

18.1: SO₃*pyr; Et₃N; DMSO

19.1: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol

20.1: HATU; Et₃N / CH₂Cl₂

With 1-methyl-pyrrolidin-2-one; hydrogenchloride; triethylsilane; potassium hydroxide; sodium hydroxide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; copper(l) iodide; 2-methyl-but-2-ene; trifuran-2-yl-phosphane; pyridine-SO₃ complex; N,N,N,N,-tetramethylethylenediamine; 2-isovalerylindane-1,3-dione; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; sec.-butyllithium; tetra(n-butyl)ammonium hydrogensulfate; 2,4-dichlorophenoxyacetic acid dimethylamine; sodium hydride; lithium triethylborohydride; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium chloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene; 7.1: Stille coupling / 9.1: Weinreb aminolysis;

DOI:10.1021/ja016616l

Reference yield:

2-amino-3-(2,3-dihydro-1H-indol-3-yl)-propionic acid methyl ester (236391-94-9) → 3a-{3-[2-tert-butoxycarbonylamino-2-(1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-ethyl]-1H-indol-7-yl}-2-(1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,8-dicarboxylic acid di-tert-butyl ester (370890-28-1)

Guidance literature:

Multi-step reaction with 19 steps

1.1: aq. Na₂CO₃ / dioxane

2.1: NaBH₄; LiCl / ethanol; tetrahydrofuran

3.1: p-TsOH / benzene

4.1: s-BuLi; TMEDA / diethyl ether / -78 °C

4.2: 73 percent / 1,2-diiodoethane / diethyl ether

5.1: DDQ; K₂CO₃ / toluene / 70 °C

6.1: (2-furyl)3P; CuI; NMP / Pd₂(dba)3*CHCl₃

7.1: DMSO / dimethylsulfoxide / 130 °C

8.1: 94 percent / Me₃Al; K₂CO₃ / CH₂Cl₂

9.1: NaH / dimethylformamide

9.2: 79 percent / dimethylformamide

10.1: 66 percent / (2-furyl)3P; PMP; DMA / Pd₂(dba)3*CHCl₃ / 90 °C

11.1: 85 percent / Bu₄NF

12.1: 95 percent / H₂ / 10 percent Pd/C / dimethylformamide / 51714.8 Torr

13.1: 1 N HCl / dioxane / 50 °C

14.1: 17 percent / 1 N NaOH; Bu₄NHSO₄ / CH₂Cl₂

15.1: LiEt₃BH / tetrahydrofuran / -78 - 0 °C

15.2: HCl / tetrahydrofuran; diethyl ether / 0 - 20 °C

16.1: KOH / methanol

17.1: SO₃*pyr; Et₃N; DMSO

18.1: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol

19.1: HATU; Et₃N / CH₂Cl₂

With 1-methyl-pyrrolidin-2-one; hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; copper(l) iodide; 2-methyl-but-2-ene; trifuran-2-yl-phosphane; pyridine-SO₃ complex; N,N,N,N,-tetramethylethylenediamine; 2-isovalerylindane-1,3-dione; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; sec.-butyllithium; tetra(n-butyl)ammonium hydrogensulfate; 2,4-dichlorophenoxyacetic acid dimethylamine; sodium hydride; lithium triethylborohydride; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium chloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene; 6.1: Stille coupling / 8.1: Weinreb aminolysis;

DOI:10.1021/ja016616l

upstream raw materials:

D-phenylalanine methyl ester hydrochloride

3a-[3-(2-tert-butoxycarbonylamino-2-carboxy-ethyl)-1H-indol-7-yl]-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 1,8-di-tert-butyl ester

3a-[3-(2-tert-butoxycarbonylamino-3-oxo-propyl)-1H-indol-7-yl]-2-formyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,8-dicarboxylic acid di-tert-butyl ester

3a-[3-(2-tert-butoxycarbonylamino-3-hydroxy-propyl)-1H-indol-7-yl]-2-hydroxymethyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,8-dicarboxylic acid di-tert-butyl ester

Downstream raw materials:

(R)-2-[((2S,3aR,8aS)-3a-{3-[(S)-2-Amino-2-((R)-1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-ethyl]-1H-indol-7-yl}-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester

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