(S)-(+)-N-benzyl-2-[[[N-(tert-butoxycarbonyl)-L-valyl]oxy]methyl]-5-nitroindoline

Base Information

• Chemical Name: (S)-(+)-N-benzyl-2-[[[N-(tert-butoxycarbonyl)-L-valyl]oxy]methyl]-5-nitroindoline
• CAS No.: 502634-03-9
• Molecular Formula: C₂₆H₃₃N₃O₆
• Molecular Weight: 483.565
• Mol file: 502634-03-9.mol

Synonyms:(S)-(+)-N-benzyl-2-[[[N-(tert-butoxycarbonyl)-L-valyl]oxy]methyl]-5-nitroindoline

Chemical Property of (S)-(+)-N-benzyl-2-[[[N-(tert-butoxycarbonyl)-L-valyl]oxy]methyl]-5-nitroindoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(+)-N-benzyl-2-[[[N-(tert-butoxycarbonyl)-L-valyl]oxy]methyl]-5-nitroindoline

There total 7 articles about (S)-(+)-N-benzyl-2-[[[N-(tert-butoxycarbonyl)-L-valyl]oxy]methyl]-5-nitroindoline 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: 53.0%

1,1-dimethylethyl S-N-(1-fluorocarbonyl-2-methylpropyl)carbamate (133010-02-3) + (S)-(-)-N-benzyl-2-(hydroxymethyl)-5-nitroindoline (502634-02-8) → (S)-(+)-N-benzyl-2-[[[N-(tert-butoxycarbonyl)-L-valyl]oxy]methyl]-5-nitroindoline (502634-03-9)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 11h;

DOI:10.1002/jhet.5570390507

Reference yield:

(S)-indoline-2-carboxylic acid (79815-20-6,78348-24-0) → (S)-(+)-N-benzyl-2-[[[N-(tert-butoxycarbonyl)-L-valyl]oxy]methyl]-5-nitroindoline (502634-03-9)

Guidance literature:

Multi-step reaction with 7 steps

1: NaBH₄; I₂ / tetrahydrofuran / 18 h / Heating

2: Na₂CO₃; EtOAc / H₂O / 4 h / 20 °C

3: Et₃N / 4 h / 20 °C

4: 65 percent / nitric acid / acetic anhydride / 0.5 h / -15 - 0 °C

5: 89 percent / aq. Na₂CO₃ / tetrahydrofuran; methanol

6: 66 percent / NaH / dimethylformamide / -30 - 20 °C

7: 53 percent / triethylamine / CH₂Cl₂ / 11 h / 20 °C

With sodium tetrahydroborate; iodine; nitric acid; sodium hydride; sodium carbonate; ethyl acetate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetic anhydride; N,N-dimethyl-formamide;

DOI:10.1002/jhet.5570390507

Reference yield:

(2S)-2,3-dihydro-1H-indole-2-ylmethanol (27640-33-1) → (S)-(+)-N-benzyl-2-[[[N-(tert-butoxycarbonyl)-L-valyl]oxy]methyl]-5-nitroindoline (502634-03-9)

Guidance literature:

Multi-step reaction with 6 steps

1: Na₂CO₃; EtOAc / H₂O / 4 h / 20 °C

2: Et₃N / 4 h / 20 °C

3: 65 percent / nitric acid / acetic anhydride / 0.5 h / -15 - 0 °C

4: 89 percent / aq. Na₂CO₃ / tetrahydrofuran; methanol

5: 66 percent / NaH / dimethylformamide / -30 - 20 °C

6: 53 percent / triethylamine / CH₂Cl₂ / 11 h / 20 °C

With nitric acid; sodium hydride; sodium carbonate; ethyl acetate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetic anhydride; N,N-dimethyl-formamide;

DOI:10.1002/jhet.5570390507

upstream raw materials:

1,1-dimethylethyl S-N-(1-fluorocarbonyl-2-methylpropyl)carbamate

(S)-(-)-N-benzyl-2-(hydroxymethyl)-5-nitroindoline

(S)-indoline-2-carboxylic acid

(2S)-2,3-dihydro-1H-indole-2-ylmethanol

Refernces