(R)-4-(N-tert-Butyloxycarbonyl)amino-N-phenylacetyltryptophan methyl ester

Base Information

Chemical Name:(R)-4-(N-tert-Butyloxycarbonyl)amino-N-phenylacetyltryptophan methyl ester
CAS No.:252289-10-4
Molecular Formula:C₂₅H₂₉N₃O₅
Molecular Weight:451.522
Hs Code.:

Synonyms:(R)-4-(N-tert-Butyloxycarbonyl)amino-N-phenylacetyltryptophan methyl ester

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Chemical Property of (R)-4-(N-tert-Butyloxycarbonyl)amino-N-phenylacetyltryptophan methyl ester

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Technology Process of (R)-4-(N-tert-Butyloxycarbonyl)amino-N-phenylacetyltryptophan methyl ester

There total 11 articles about (R)-4-(N-tert-Butyloxycarbonyl)amino-N-phenylacetyltryptophan methyl 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:

: 87-52-5
3-(Dimethylaminomethyl)indole

: 252289-10-4
(R)-4-(N-tert-Butyloxycarbonyl)amino-N-phenylacetyltryptophan methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: NaH / various solvent(s); tetrahydrofuran / 3 h / 0 °C

1.2: 84.9 percent / various solvent(s); tetrahydrofuran / 0 °C

2.1: tBuLi / diethyl ether / 1.75 h / -78 - 0 °C

2.2: 73 percent / diethyl ether / 1 h / -78 °C

3.1: 91.7 percent / tetrahydrofuran / 20 °C

4.1: MeI / dimethylformamide / 20 °C

5.1: 6.51 g / TBAF / tetrahydrofuran / 1 h / 20 °C

6.1: morpholine / Pd[PPh₃]4 / tetrahydrofuran / 0.5 h / 20 °C

7.1: 3.42 g / dioxane / 0.5 h / Heating

8.1: aq. NaOH; penicillin G acylase / aq. methanol / 37 °C / pH 7.6

9.1: CH₂Cl₂ / 0.5 h / 20 °C

With morpholine; sodium hydroxide; penicillin G acylase; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hydride; methyl iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 5.1: Mannich-type reaction;
DOI:10.1002/1521-3765(20001103)6:21<3943::AID-CHEM3943<3.3.CO;2-K

Reference yield:

: 88744-17-6
phenylacetylaminomalonic acid diethyl ester

: 252289-10-4
(R)-4-(N-tert-Butyloxycarbonyl)amino-N-phenylacetyltryptophan methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 79 percent / LiCl; DBU; 4 Angstroem molecular sieves / tetrahydrofuran; CH₂Cl₂ / Heating

2: 6.51 g / TBAF / tetrahydrofuran / 1 h / 20 °C

3: morpholine / Pd[PPh₃]4 / tetrahydrofuran / 0.5 h / 20 °C

4: 3.42 g / dioxane / 0.5 h / Heating

5: aq. NaOH; penicillin G acylase / aq. methanol / 37 °C / pH 7.6

6: CH₂Cl₂ / 0.5 h / 20 °C

With morpholine; sodium hydroxide; penicillin G acylase; 4 A molecular sieve; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; 2: Mannich-type reaction;
DOI:10.1002/1521-3765(20001103)6:21<3943::AID-CHEM3943<3.3.CO;2-K

Reference yield:

: 146886-51-3
1-(N-triisopropylsilyl-1H-indol-3-yl)-N,N-dimethylmethanamine

: 252289-10-4
(R)-4-(N-tert-Butyloxycarbonyl)amino-N-phenylacetyltryptophan methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: tBuLi / diethyl ether / 1.75 h / -78 - 0 °C

1.2: 73 percent / diethyl ether / 1 h / -78 °C

2.1: 91.7 percent / tetrahydrofuran / 20 °C

3.1: MeI / dimethylformamide / 20 °C

4.1: 6.51 g / TBAF / tetrahydrofuran / 1 h / 20 °C

5.1: morpholine / Pd[PPh₃]4 / tetrahydrofuran / 0.5 h / 20 °C

6.1: 3.42 g / dioxane / 0.5 h / Heating

7.1: aq. NaOH; penicillin G acylase / aq. methanol / 37 °C / pH 7.6

8.1: CH₂Cl₂ / 0.5 h / 20 °C

With morpholine; sodium hydroxide; penicillin G acylase; tetrabutyl ammonium fluoride; tert.-butyl lithium; methyl iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 4.1: Mannich-type reaction;
DOI:10.1002/1521-3765(20001103)6:21<3943::AID-CHEM3943<3.3.CO;2-K