methyl (R)-2-(benzyloxycarbonylamino)-2-(6-methyl-1H-indol-3-yl)-2-phenylacetate

Base Information

Chemical Name:methyl (R)-2-(benzyloxycarbonylamino)-2-(6-methyl-1H-indol-3-yl)-2-phenylacetate
CAS No.:1360863-49-5
Molecular Formula:C₂₆H₂₄N₂O₄
Molecular Weight:428.488
Hs Code.:

Synonyms:methyl (R)-2-(benzyloxycarbonylamino)-2-(6-methyl-1H-indol-3-yl)-2-phenylacetate

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Chemical Property of methyl (R)-2-(benzyloxycarbonylamino)-2-(6-methyl-1H-indol-3-yl)-2-phenylacetate

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Technology Process of methyl (R)-2-(benzyloxycarbonylamino)-2-(6-methyl-1H-indol-3-yl)-2-phenylacetate

There total 3 articles about methyl (R)-2-(benzyloxycarbonylamino)-2-(6-methyl-1H-indol-3-yl)-2-phenylacetate 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: 99.0%

: 3420-02-8
6-methylindole

: 1360863-29-1
methyl (Z)-2-(benzyloxycarbonylimino)-2-phenylacetate

: 1360863-49-5
methyl (R)-2-(benzyloxycarbonylamino)-2-(6-methyl-1H-indol-3-yl)-2-phenylacetate

Guidance literature:: With (S)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; In toluene; at -5 ℃; for 24h; optical yield given as %ee; enantioselective reaction; Inert atmosphere; Molecular sieve;
DOI:10.1002/adsc.201100615

Reference yield:

: 621-84-1
O-benzyl carbamate

: 1360863-49-5
methyl (R)-2-(benzyloxycarbonylamino)-2-(6-methyl-1H-indol-3-yl)-2-phenylacetate

Guidance literature:: Multi-step reaction with 2 steps

1.1: dirhodium tetraacetate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / Inert atmosphere; Molecular sieve; Reflux

1.2: 1.5 h / 20 °C / Inert atmosphere

2.1: (S)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate / toluene / 24 h / -5 °C / Inert atmosphere; Molecular sieve

With dirhodium tetraacetate; (S)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; toluene; 2.1: Friedel-Crafts reaction;
DOI:10.1002/adsc.201100615

Reference yield:

: 22979-35-7
Methyl phenyldiazoacetate

: 1360863-49-5
methyl (R)-2-(benzyloxycarbonylamino)-2-(6-methyl-1H-indol-3-yl)-2-phenylacetate

Guidance literature:: Multi-step reaction with 2 steps

1.1: dirhodium tetraacetate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / Inert atmosphere; Molecular sieve; Reflux

1.2: 1.5 h / 20 °C / Inert atmosphere

2.1: (S)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate / toluene / 24 h / -5 °C / Inert atmosphere; Molecular sieve

With dirhodium tetraacetate; (S)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; toluene; 2.1: Friedel-Crafts reaction;
DOI:10.1002/adsc.201100615