(S,S)-(2-(4-((1-(((phenylmethyl)oxy)carbonyl)-2-methylpropyl)amino)-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester

Base Information

• Chemical Name: (S,S)-(2-(4-((1-(((phenylmethyl)oxy)carbonyl)-2-methylpropyl)amino)-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester
• CAS No.: 131442-94-9
• Molecular Formula: C₃₁H₃₅N₃O₅
• Molecular Weight: 529.636
• Mol file: 131442-94-9.mol

Synonyms:(S,S)-(2-(4-((1-(((phenylmethyl)oxy)carbonyl)-2-methylpropyl)amino)-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester

Chemical Property of (S,S)-(2-(4-((1-(((phenylmethyl)oxy)carbonyl)-2-methylpropyl)amino)-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,S)-(2-(4-((1-(((phenylmethyl)oxy)carbonyl)-2-methylpropyl)amino)-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester

There total 27 articles about (S,S)-(2-(4-((1-(((phenylmethyl)oxy)carbonyl)-2-methylpropyl)amino)-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl 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: 80.0%

benzyl (R)-4-methyl-2-(trifluoromethylsulfonyloxy)pentanoate (131423-64-8) + (S)-(2-(4-amino-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester (110815-32-2) → (S,S)-(2-(4-((1-(((phenylmethyl)oxy)carbonyl)-2-methylpropyl)amino)-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester (131442-94-9)

Guidance literature:

With 2,6-dimethylpyridine; In 1,2-dichloro-ethane; at 70 ℃; for 18h;

DOI:10.1002/1521-3765(20001103)6:21<3943::AID-CHEM3943<3.3.CO;2-K

Reference yield: 73.0%

(S)-2-[3-((R)-3-Acetoxy-2-benzyloxycarbonylamino-propionyl)-1H-indol-4-ylamino]-3-methyl-butyric acid benzyl ester → (S,S)-(2-(4-((1-(((phenylmethyl)oxy)carbonyl)-2-methylpropyl)amino)-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester (131442-94-9)

Guidance literature:

With sodium tetrahydroborate; In water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)87853-4

Reference yield:

1-(N-triisopropylsilyl-1H-indol-3-yl)-N,N-dimethylmethanamine (146886-51-3) → (S,S)-(2-(4-((1-(((phenylmethyl)oxy)carbonyl)-2-methylpropyl)amino)-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester (131442-94-9)

Guidance literature:

Multi-step reaction with 12 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: 39 percent / aq. NaOH; penicillin G acylase / aq. methanol / 37 °C / pH 7.6

8.1: dioxane; aq. NaOH / 1 h / 20 °C

9.1: 0.903 g / methanol; CH₂Cl₂ / 0.5 h / 20 °C

10.1: 91.4 percent / CF₃COOH / various solvent(s) / 0.5 h / 20 °C

11.1: 89.9 percent / LiBH₄ / tetrahydrofuran / 2 h / Heating

12.1: 80 percent / 2,6-lutidine / 1,2-dichloro-ethane / 18 h / 70 °C

With morpholine; 2,6-dimethylpyridine; sodium hydroxide; lithium borohydride; penicillin G acylase; tetrabutyl ammonium fluoride; tert.-butyl lithium; trifluoroacetic acid; methyl iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; sodium hydroxide; diethyl ether; dichloromethane; 1,2-dichloro-ethane; 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

upstream raw materials:

benzyl (R)-4-methyl-2-(trifluoromethylsulfonyloxy)pentanoate

(S)-(2-(4-amino-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester

3-(Dimethylaminomethyl)indole

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

Downstream raw materials:

indolactam V

6-((10S,13S)-10-Isopropyl-11-oxo-3,9,12-triaza-tricyclo[6.6.1.0^4,15]pentadeca-1,4,6,8⁽¹⁵⁾-tetraen-13-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester