N-(methylcarbamoyl)homotyrosine methyl ester

Base Information

• Chemical Name: N-(methylcarbamoyl)homotyrosine methyl ester
• CAS No.: 110936-12-4
• Molecular Formula: C₁₃H₁₇NO₅
• Molecular Weight: 267.282
• Mol file: 110936-12-4.mol

Synonyms:N-(methylcarbamoyl)homotyrosine methyl ester

Chemical Property of N-(methylcarbamoyl)homotyrosine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-(methylcarbamoyl)homotyrosine methyl ester

There total 4 articles about N-(methylcarbamoyl)homotyrosine methyl 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: 80.0%

(2Z)-2-<(methoxycarbonyl)amino>-4-(4-methoxyphenyl)but-2-enoic acid (110971-27-2) → N-(methylcarbamoyl)homotyrosine methyl ester (110936-12-4) + (2R)-2-<(methoxycarbonyl)amino>-4-(4-methoxyphenyl)-butanoic acid (110936-09-9)

Guidance literature:

With [Rh(bicyclo[2.2.1]hepta-2,5-diene)((2S,3S)-(-)-2,3-bis(diphenylphosphino)butane)]ClO₄; hydrogen; sodium acetate; In methanol; at 20 ℃; for 96h; under 2068.6 Torr; Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00232a016

Reference yield:

para-iodoanisole (696-62-8) → N-(methylcarbamoyl)homotyrosine methyl ester (110936-12-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 49 percent / aq. NaHCO₃, Pd(OAc)2, Bu₄NCl / 24 h / 45 °C

2: H₂ / 10 percent Pd/C / methanol / 4 h / Ambient temperature

3: aq. NaHCO₃ / dioxane / 5 h / Ambient temperature

With palladium diacetate; tetrabutyl-ammonium chloride; hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In 1,4-dioxane; methanol;

DOI:10.1248/cpb.46.1094

Reference yield:

-2-<(benzyloxycarbonyl)amino>-4-(4-methoxyphenyl)-3-butenoic acid (171077-29-5) → N-(methylcarbamoyl)homotyrosine methyl ester (110936-12-4)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10 percent Pd/C / methanol / 4 h / Ambient temperature

2: aq. NaHCO₃ / dioxane / 5 h / Ambient temperature

With hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In 1,4-dioxane; methanol;

DOI:10.1248/cpb.46.1094

upstream raw materials:

(2Z)-2-<(methoxycarbonyl)amino>-4-(4-methoxyphenyl)but-2-enoic acid

O-methyl-L-homotyrosine

methyl chloroformate

para-iodoanisole

Downstream raw materials:

L-homotyrosine hydrobromide

(2S,3S,4S)-3-hydroxy-4-methyl-ProOMe-Thr-Homotyr-4-OH-Pro-Thr-α-N-(octyloxybenzoyl)-δ-CBZ-Orn

(2S,3S,4S)-3-hydroxy-4-methyl-Pro-Thr-Homotyr-4-OH-Pro-Thr-α-N-(octyloxybenzoyl)-δ-CBZ-Orn

Thr-O-CBZ-Homotyr-4-OH-Pro-Thr-α-N-(octyloxybenzoyl)-δ-CBZ-Orn

Refernces

• 1、 Itaya,Shimizu. "The Heck reaction of N-protected vinylglycines with 4-iodoanisole". . p. 398 - 402. Retrieved 2007/10/02.