(2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide

Base Information

• Chemical Name: (2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide
• CAS No.: 81902-59-2
• Molecular Formula: C₁₉H₂₈BrNO₆
• Molecular Weight: 446.338

Synonyms:(2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide

Chemical Property of (2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide

Chemical Property:

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Technology Process of (2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide

There total 4 articles about (2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide 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: 86.0%

(2,4-dimethoxy-benzylamino)-acetic acid (20839-79-6) + (2S,3R)-2-Bromo-3-hydroxybutanoic acid (70702-03-3) → (2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide (81902-59-2)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20 ℃; for 0.25h;

DOI:10.1016/S0040-4039(01)92460-8

Reference yield: 84.0%

(2S,3R)-2-Bromo-3-hydroxybutanoic acid (70702-03-3) + t-butyl N-(2,4-dimethoxybenzyl)glycinate (81902-60-5) → (2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide (81902-59-2)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20 - 25 ℃; for 0.25h;

DOI:10.1016/S0040-4020(01)91132-9

Reference yield:

bromoacetic acid tert-butyl ester (5292-43-3) → (2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide (81902-59-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / Et₃N / tetrahydrofuran / 1 h / Heating

2: 84 percent / N,N-dicyclohexylcarbodiimide / tetrahydrofuran / 0.25 h / 20 - 25 °C

With triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)91132-9

upstream raw materials:

(2,4-dimethoxy-benzylamino)-acetic acid

(2S,3R)-2-Bromo-3-hydroxybutanoic acid

t-butyl N-(2,4-dimethoxybenzyl)glycinate

bromoacetic acid tert-butyl ester

Downstream raw materials:

<3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-acetyl-2-azetidinone

(3S,4R)-3-<(R)-1-hydroxyethyl>-4-<(benzyloxycarbonyl)methyl>-2-azetidinone

[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(2,4-dimethoxy-benzyl)-4-oxo-azetidin-2-yl]-acetic acid methyl ester

<3S-<3α(S^*),4α>>-t-butyl 1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-2-azetidinone-4-carboxylate

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