[[3-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-1H-indol-4-yl]-(4-nitro-benzyloxycarbonyl)-amino]-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester

Base Information

Chemical Name:[[3-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-1H-indol-4-yl]-(4-nitro-benzyloxycarbonyl)-amino]-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester
CAS No.:84590-38-5
Molecular Formula:C₃₀H₃₃N₅O₁₁
Molecular Weight:639.619
Hs Code.:

[[3-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-1H-indol-4-yl]-(4-nitro-benzyloxycarbonyl)-amino]-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester

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Chemical Property of [[3-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-1H-indol-4-yl]-(4-nitro-benzyloxycarbonyl)-amino]-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester

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Technology Process of [[3-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-1H-indol-4-yl]-(4-nitro-benzyloxycarbonyl)-amino]-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester

There total 13 articles about [[3-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-1H-indol-4-yl]-(4-nitro-benzyloxycarbonyl)-amino]-acetic acid 2,5-dioxo-pyrrolidin-1-yl 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: 74.0%

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

: 84590-37-4
[[3-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-1H-indol-4-yl]-(4-nitro-benzyloxycarbonyl)-amino]-acetic acid

: 84590-38-5
[[3-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-1H-indol-4-yl]-(4-nitro-benzyloxycarbonyl)-amino]-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester

Guidance literature:: With dicyclohexyl-carbodiimide; In acetonitrile; for 2h; Ambient temperature;
DOI:10.1248/cpb.30.3457

Reference yield:

: 1070-19-5
N-(tert-butyloxycarbonyl) azide

: 84590-38-5
[[3-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-1H-indol-4-yl]-(4-nitro-benzyloxycarbonyl)-amino]-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: NaHCO₃ / dioxane; H₂O / 40 h / 45 °C

2: 100 percent / lithium borohydride / tetrahydrofuran / 2 h / Ambient temperature

3: 87 percent / H₂ / Pd-charcoal / ethanol

4: 72 percent / NaHCO₃ / ethanol / 1 h / Heating

5: 95 percent / NaHCO₃ / diethyl ether; H₂O / 3 h / Ambient temperature

6: 98 percent / 2N KOH / methanol

7: 74 percent / DCC / acetonitrile / 2 h / Ambient temperature

With potassium hydroxide; lithium borohydride; hydrogen; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; water; acetonitrile;
DOI:10.1248/cpb.30.3457

Reference yield:

: 91768-84-2
N-acetyl-4-nitrotryptophan

: 84590-38-5
[[3-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-1H-indol-4-yl]-(4-nitro-benzyloxycarbonyl)-amino]-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: SOCl₂ / 0 deg C, 1 h, 60 deg C, 3 h

2: HCl / ethanol / 48 h

3: NaHCO₃ / dioxane; H₂O / 40 h / 45 °C

4: 100 percent / lithium borohydride / tetrahydrofuran / 2 h / Ambient temperature

5: 87 percent / H₂ / Pd-charcoal / ethanol

6: 72 percent / NaHCO₃ / ethanol / 1 h / Heating

7: 95 percent / NaHCO₃ / diethyl ether; H₂O / 3 h / Ambient temperature

8: 98 percent / 2N KOH / methanol

9: 74 percent / DCC / acetonitrile / 2 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; lithium borohydride; thionyl chloride; hydrogen; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; water; acetonitrile;
DOI:10.1248/cpb.30.3457