methyl 3-(1,3-dioxoisoindolin-2-yl)-2-(4-(triisopropylsilyloxy)phenyl)propanoate

Base Information

• Chemical Name: methyl 3-(1,3-dioxoisoindolin-2-yl)-2-(4-(triisopropylsilyloxy)phenyl)propanoate
• CAS No.: 1253954-99-2
• Molecular Formula: C₂₇H₃₅NO₅Si
• Molecular Weight: 481.664

Synonyms:methyl 3-(1,3-dioxoisoindolin-2-yl)-2-(4-(triisopropylsilyloxy)phenyl)propanoate

Chemical Property of methyl 3-(1,3-dioxoisoindolin-2-yl)-2-(4-(triisopropylsilyloxy)phenyl)propanoate

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Technology Process of methyl 3-(1,3-dioxoisoindolin-2-yl)-2-(4-(triisopropylsilyloxy)phenyl)propanoate

There total 3 articles about methyl 3-(1,3-dioxoisoindolin-2-yl)-2-(4-(triisopropylsilyloxy)phenyl)propanoate 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: 68.0%

N-(bromomethyl)phtalimide (5332-26-3) + methyl 2-(4-(triisopropylsilyloxy)phenyl)acetate (243641-04-5) → methyl 3-(1,3-dioxoisoindolin-2-yl)-2-(4-(triisopropylsilyloxy)phenyl)propanoate (1253954-99-2)

Guidance literature:

methyl 2-(4-(triisopropylsilyloxy)phenyl)acetate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

N-(bromomethyl)phtalimide; In tetrahydrofuran; at -78 ℃; for 2h; Cooling with ice;

Reference yield:

Methyl 4-hydroxyphenylacetate (14199-15-6) → methyl 3-(1,3-dioxoisoindolin-2-yl)-2-(4-(triisopropylsilyloxy)phenyl)propanoate (1253954-99-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,6-dimethylpyridine / dichloromethane

2: lithium hexamethyldisilazane / tetrahydrofuran / -78 - 0 °C

With 2,6-dimethylpyridine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmcl.2016.03.104

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → methyl 3-(1,3-dioxoisoindolin-2-yl)-2-(4-(triisopropylsilyloxy)phenyl)propanoate (1253954-99-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,6-dimethylpyridine / dichloromethane

2: lithium hexamethyldisilazane / tetrahydrofuran / -78 - 0 °C

With 2,6-dimethylpyridine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmcl.2016.03.104

upstream raw materials:

N-(bromomethyl)phtalimide

methyl 2-(4-(triisopropylsilyloxy)phenyl)acetate

Methyl 4-hydroxyphenylacetate

triisopropylsilyl trifluoromethanesulfonate

Downstream raw materials:

2-(2-carboxy-2-(4-(triisopropylsilyloxy)phenyl)ethylcarbamoyl)benzoic acid

3-(1,3-dioxoisoindolin-2-yl)-N-(isoquinolin-6-yl)-2-(4-(triisopropylsilyloxy)phenyl)propanamide

tert-butyl 3-(isoquinolin-6-ylamino)-3-oxo-2-(4-(triisopropylsilyloxy)phenyl)propylcarbamate

tert-butyl 2-(4-hydroxyphenyl)-3-(isoquinolin-6-ylamino)-3-oxopropylcarbamate

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