3-Oxazolidinecarboxylic acid, 4-[[3-[(3S)-7-bromo-2,3-dihydro-3-(hydroxymethyl)-2-oxo-1H-indol-3-yl]- 4-hydroxyphenyl]methyl]-2,2-dimethyl-, phenylmethyl ester, (4S)-

Base Information

Chemical Name:3-Oxazolidinecarboxylic acid, 4-[[3-[(3S)-7-bromo-2,3-dihydro-3-(hydroxymethyl)-2-oxo-1H-indol-3-yl]- 4-hydroxyphenyl]methyl]-2,2-dimethyl-, phenylmethyl ester, (4S)-
CAS No.:570377-06-9
Molecular Formula:C29H29BrN2O6
Molecular Weight:581.463
Hs Code.:

3-Oxazolidinecarboxylic acid,
4-[[3-[(3S)-7-bromo-2,3-dihydro-3-(hydroxymethyl)-2-oxo-1H-indol-3-yl]-
4-hydroxyphenyl]methyl]-2,2-dimethyl-, phenylmethyl ester, (4S)-

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Chemical Property of 3-Oxazolidinecarboxylic acid, 4-[[3-[(3S)-7-bromo-2,3-dihydro-3-(hydroxymethyl)-2-oxo-1H-indol-3-yl]- 4-hydroxyphenyl]methyl]-2,2-dimethyl-, phenylmethyl ester, (4S)-

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Technology Process of 3-Oxazolidinecarboxylic acid, 4-[[3-[(3S)-7-bromo-2,3-dihydro-3-(hydroxymethyl)-2-oxo-1H-indol-3-yl]- 4-hydroxyphenyl]methyl]-2,2-dimethyl-, phenylmethyl ester, (4S)-

There total 11 articles about 3-Oxazolidinecarboxylic acid, 4-[[3-[(3S)-7-bromo-2,3-dihydro-3-(hydroxymethyl)-2-oxo-1H-indol-3-yl]- 4-hydroxyphenyl]methyl]-2,2-dimethyl-, phenylmethyl ester, (4S)- 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: 70.0%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 570377-05-8
4-[3-(7-bromo-2-oxo-2,3-dihydro-1H-indol-3-yl)-4-hydroxy-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

: 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

Guidance literature:: 4-[3-(7-bromo-2-oxo-2,3-dihydro-1H-indol-3-yl)-4-hydroxy-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester; With chloro-trimethyl-silane; triethylamine; In dichloromethane; at 0 ℃; for 1.5h;

formaldehyd; With ytterbium(III) triflate; In tetrahydrofuran; at 25 ℃; for 24h;
DOI:10.1002/anie.200351112

Reference yield:

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 793724-28-4
4-[3-(7-bromo-2-trimethylsilanyloxy-1H-indol-3-yl)-4-hydroxy-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

: 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

Guidance literature:: With ytterbium(III) triflate; In tetrahydrofuran; at 25 ℃; for 24h;
DOI:10.1021/ja040093a

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 7 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

With 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