N_α-methyl>thio>acetyl>ACHPA>Ile N-<(4-amino-2-methyl-5-pyrimidinyl)methyl>amide

Base Information

• Chemical Name: N_α-methyl>thio>acetyl>ACHPA>Ile N-<(4-amino-2-methyl-5-pyrimidinyl)methyl>amide
• CAS No.: 136658-80-5
• Molecular Formula: C₄₃H₆₇N₇O₇S
• Molecular Weight: 826.114

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Chemical Property of N_α-methyl>thio>acetyl>ACHPA>Ile N-<(4-amino-2-methyl-5-pyrimidinyl)methyl>amide

Chemical Property:

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Technology Process of N_α-methyl>thio>acetyl>ACHPA>Ile N-<(4-amino-2-methyl-5-pyrimidinyl)methyl>amide

There total 14 articles about N_α-methyl>thio>acetyl>ACHPA>Ile N-<(4-amino-2-methyl-5-pyrimidinyl)methyl>amide 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: 76.0%

H-ACHPA-Ile N-<(4-amino-2-methyl-5-pyrimidinyl)methyl>amide dihydrochloride (136735-33-6) + 2-<<<(4S,5R)-4-benzyl-2,2-dimethyl-5-oxazolidinyl>methyl>thio>acetic acid (136630-90-5) → Nα-methyl>thio>acetyl>ACHPA>Ile N-<(4-amino-2-methyl-5-pyrimidinyl)methyl>amide (136658-80-5,136735-32-5)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 14h; Ambient temperature;

DOI:10.1021/jm00115a016

Reference yield: 49.0%

H-ACHPA-Ile N-<(4-amino-2-methyl-5-pyrimidinyl)methyl>amide dihydrochloride (136735-33-6) + 2-<<<(4S,5S)-4-benzyl-2,2-dimethyl-5-oxazolidinyl>methyl>thio>acetic acid (136630-91-6) → Nα-methyl>thio>acetyl>ACHPA>Ile N-<(4-amino-2-methyl-5-pyrimidinyl)methyl>amide (136658-80-5,136735-32-5)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 14h; Ambient temperature;

DOI:10.1021/jm00115a016

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → Nα-methyl>thio>acetyl>ACHPA>Ile N-<(4-amino-2-methyl-5-pyrimidinyl)methyl>amide (136658-80-5,136735-32-5)

Guidance literature:

Multi-step reaction with 7 steps

1: N-methylmorpholine (NMM) / ethyl acetate / 0.17 h / -10 °C

2: diethyl ether / 3 h / Ambient temperature

3: 47percent aq. HBr / dioxane / 1 h / 0 °C

4: 76 percent / sodium borohydride / methanol / 1 h / 0 °C

5: 88 percent / p-toluenesulfonic acid / CH₂Cl₂ / 36 h / Ambient temperature

6: 1.) NaOMe, 2.) KI / 1.) MeOH, RT, 30 min, 2.) MeOH, RT, 36 h

7: 49 percent / N-methylmorpholine (NMM), 1-hydroxybenzotriazole (HOBT), N-ethyl-N'-<3-(dimethylamino)propyl>carbodiimide hydrochloride (EDCI) / dimethylformamide / 14 h / Ambient temperature

With 4-methyl-morpholine; sodium tetrahydroborate; hydrogen bromide; sodium methylate; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; potassium iodide; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00115a016

upstream raw materials:

H-ACHPA-Ile N-<(4-amino-2-methyl-5-pyrimidinyl)methyl>amide dihydrochloride

2-<<<(4S,5S)-4-benzyl-2,2-dimethyl-5-oxazolidinyl>methyl>thio>acetic acid

N-tert-butoxycarbonyl-L-phenylalanine

tert-butyl 4-bromo-3-oxo-1-phenylbutan-2-ylcarbamate

Downstream raw materials:

BOC-PheΨ<(R)-CHOHCH2S>Gly-ACHPA-Ile N-<(4-amino-2-methyl-5-pyrimidinyl)methyl>amide

BOC-PheΨ<(S)-CHOHCH2S>Gly-ACHPA-Ile N-<(4-amino-2-methyl-5-pyrimidinyl)methyl>amide

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