4-[3-[7-bromo-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-(tert-butyl-dimethyl-silanyloxy)-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Base Information

Chemical Name:4-[3-[7-bromo-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-(tert-butyl-dimethyl-silanyloxy)-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester
CAS No.:570377-14-9
Molecular Formula:C₄₁H₅₇BrN₂O₆Si₂
Molecular Weight:809.988
Hs Code.:

4-[3-[7-bromo-3-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-2-oxo-2,3-dihydro-1<i>H</i>-indol-3-yl]-4-(<i>tert</i>-butyl-dimethyl-silanyloxy)-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Synonyms:4-[3-[7-bromo-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-(tert-butyl-dimethyl-silanyloxy)-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

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Chemical Property of 4-[3-[7-bromo-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-(tert-butyl-dimethyl-silanyloxy)-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

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Technology Process of 4-[3-[7-bromo-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-(tert-butyl-dimethyl-silanyloxy)-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

There total 11 articles about 4-[3-[7-bromo-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-(tert-butyl-dimethyl-silanyloxy)-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl 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: 84.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 570377-06-9
4-[3-(7-bromo-3-hydroxymethyl-2-oxo-2,3-dihydro-1H-indol-3-yl)-4-hydroxy-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

: 570377-14-9
4-[3-[7-bromo-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-(tert-butyl-dimethyl-silanyloxy)-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Guidance literature:: With 1H-imidazole; In dichloromethane; at 25 ℃; for 6h;
DOI:10.1002/anie.200351112 DOI:10.1021/ja040093a

Reference yield:

: 13512-31-7
N-(benzyloxycarbonyl)-L-tyrosine methyl ester

: 570377-14-9
4-[3-[7-bromo-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-(tert-butyl-dimethyl-silanyloxy)-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 21.8 g / TiCl₄ / CH₂Cl₂ / 6 h / 25 °C

2: SOCl₂ / 10 h / 25 °C

3: 15.7 g / NaCNBH₃ / acetonitrile / 5 h / 25 °C

4: 97 percent / LiBH₄ / tetrahydrofuran / 2 h / 25 °C

5: 98 percent / p-TsOH / acetone / 2 h / 25 °C

6: Et₃N / CH₂Cl₂ / 2 h / 0 °C

7: 7.38 g / aq. Yb(OTf)3 / tetrahydrofuran / 24 h / 25 °C

8: 84 percent / imidazole / CH₂Cl₂ / 6 h / 25 °C

With 1H-imidazole; lithium borohydride; thionyl chloride; titanium tetrachloride; sodium cyanoborohydride; toluene-4-sulfonic acid; triethylamine; ytterbium(III) triflate; In tetrahydrofuran; dichloromethane; acetone; acetonitrile; 1: Fridel-Crafts reaction;
DOI:10.1021/ja040093a

Reference yield:

: 570377-13-8
{2-[3-(7-bromo-2-oxo-2,3-dihydro-1H-indol-3-yl)-4-hydroxy-phenyl]-1-hydroxymethyl-ethyl}-carbamic acid benzyl ester

: 570377-14-9
4-[3-[7-bromo-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-(tert-butyl-dimethyl-silanyloxy)-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / p-TsOH / acetone / 2 h / 25 °C

2: Et₃N / CH₂Cl₂ / 2 h / 0 °C

3: 7.38 g / aq. Yb(OTf)3 / tetrahydrofuran / 24 h / 25 °C

4: 84 percent / imidazole / CH₂Cl₂ / 6 h / 25 °C

With 1H-imidazole; toluene-4-sulfonic acid; triethylamine; ytterbium(III) triflate; In tetrahydrofuran; dichloromethane; acetone;
DOI:10.1021/ja040093a