(2R)-N₁-[(1S)-2,2-dimethyl-1-({[(1S)-2-methoxy-1-phenylethyl]amino}carbonyl)propyl]-2-{3-(3-methyl-4-phenylphenyl)propyl}-(N₄-3-propenyloxy)butanediamide

Base Information

• Chemical Name: (2R)-N₁-[(1S)-2,2-dimethyl-1-({[(1S)-2-methoxy-1-phenylethyl]amino}carbonyl)propyl]-2-{3-(3-methyl-4-phenylphenyl)propyl}-(N₄-3-propenyloxy)butanediamide
• CAS No.: 230961-47-4
• Molecular Formula: C₃₈H₄₉N₃O₅
• Molecular Weight: 627.824

Synonyms:(2R)-N₁-[(1S)-2,2-dimethyl-1-({[(1S)-2-methoxy-1-phenylethyl]amino}carbonyl)propyl]-2-{3-(3-methyl-4-phenylphenyl)propyl}-(N₄-3-propenyloxy)butanediamide

Chemical Property of (2R)-N₁-[(1S)-2,2-dimethyl-1-({[(1S)-2-methoxy-1-phenylethyl]amino}carbonyl)propyl]-2-{3-(3-methyl-4-phenylphenyl)propyl}-(N₄-3-propenyloxy)butanediamide

Chemical Property:

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Technology Process of (2R)-N₁-[(1S)-2,2-dimethyl-1-({[(1S)-2-methoxy-1-phenylethyl]amino}carbonyl)propyl]-2-{3-(3-methyl-4-phenylphenyl)propyl}-(N₄-3-propenyloxy)butanediamide

There total 25 articles about (2R)-N₁-[(1S)-2,2-dimethyl-1-({[(1S)-2-methoxy-1-phenylethyl]amino}carbonyl)propyl]-2-{3-(3-methyl-4-phenylphenyl)propyl}-(N₄-3-propenyloxy)butanediamide 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%

O-allylhydroxylamine hydrochloride (38945-21-0) + UK-370106 (230961-21-4) → (2R)-N1-[(1S)-2,2-dimethyl-1-({[(1S)-2-methoxy-1-phenylethyl]amino}carbonyl)propyl]-2-{3-(3-methyl-4-phenylphenyl)propyl}-(N4-3-propenyloxy)butanediamide (230961-47-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jm0308038

Reference yield:

3-methyl-4-phenylbromobenzene (5002-26-6) → (2R)-N1-[(1S)-2,2-dimethyl-1-({[(1S)-2-methoxy-1-phenylethyl]amino}carbonyl)propyl]-2-{3-(3-methyl-4-phenylphenyl)propyl}-(N4-3-propenyloxy)butanediamide (230961-47-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: Mg; I₂ / tetrahydrofuran / Heating

1.2: 60 percent / tetrahydrofuran / -40 - 0 °C

2.1: Et₃SiH; TFA / 0 - 20 °C

3.1: (COCl)2; DMF / CH₂Cl₂ / -10 - 20 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -70 - -50 °C

4.2: 91 percent / tetrahydrofuran; hexane / -70 - 0 °C

5.1: NaN(SiMe₃)2 / tetrahydrofuran / 1 h / -75 °C

5.2: 61 percent / tetrahydrofuran / -70 - -50 °C

6.1: 97 percent / aq. H₂O₂; LiOH / tetrahydrofuran / 0 - 20 °C

7.1: 99 percent / N-(dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; i-Pr₂NEt; 1-hydroxy-1,2,3-benzotriazole hydrate / CH₂Cl₂ / 4 - 20 °C

8.1: 80 percent / TFA / CH₂Cl₂ / 2 h / 20 °C

9.1: 80 percent / i-Pr₂NEt; PyAOP / CH₂Cl₂ / 0 - 20 °C

With triethylsilane; lithium hydroxide; n-butyllithium; oxalyl dichloride; dihydrogen peroxide; iodine; sodium hexamethyldisilazane; magnesium; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jm0308038

Reference yield:

(S)-2-methoxy-1-phenylethylamine (91298-74-7) → (2R)-N1-[(1S)-2,2-dimethyl-1-({[(1S)-2-methoxy-1-phenylethyl]amino}carbonyl)propyl]-2-{3-(3-methyl-4-phenylphenyl)propyl}-(N4-3-propenyloxy)butanediamide (230961-47-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 81 percent / N-(dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; N-methylmorpholine; 1-hydroxy-1,2,3-benzotriazole hydrate / CH₂Cl₂ / 2 - 20 °C

2: 97 percent / HCl(gas) / CH₂Cl₂; dioxane / 4 - 20 °C

3: 99 percent / N-(dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; i-Pr₂NEt; 1-hydroxy-1,2,3-benzotriazole hydrate / CH₂Cl₂ / 4 - 20 °C

4: 80 percent / TFA / CH₂Cl₂ / 2 h / 20 °C

5: 80 percent / i-Pr₂NEt; PyAOP / CH₂Cl₂ / 0 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In 1,4-dioxane; dichloromethane;

DOI:10.1021/jm0308038

upstream raw materials:

O-allylhydroxylamine hydrochloride

UK-370106

glutaric anhydride,

3-methyl-4-phenylbromobenzene

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