5-benzyloxy-4(S)-methyl-2(R)-[2-(4-n-propylphenyl)ethyl]pentanoic acid 1-[(S)-tert-butylglycine phenylamide] amide

Base Information

• Chemical Name: 5-benzyloxy-4(S)-methyl-2(R)-[2-(4-n-propylphenyl)ethyl]pentanoic acid 1-[(S)-tert-butylglycine phenylamide] amide
• CAS No.: 189217-66-1
• Molecular Formula: C₃₆H₄₈N₂O₃
• Molecular Weight: 556.789

Synonyms:5-benzyloxy-4(S)-methyl-2(R)-[2-(4-n-propylphenyl)ethyl]pentanoic acid 1-[(S)-tert-butylglycine phenylamide] amide

Chemical Property of 5-benzyloxy-4(S)-methyl-2(R)-[2-(4-n-propylphenyl)ethyl]pentanoic acid 1-[(S)-tert-butylglycine phenylamide] amide

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Technology Process of 5-benzyloxy-4(S)-methyl-2(R)-[2-(4-n-propylphenyl)ethyl]pentanoic acid 1-[(S)-tert-butylglycine phenylamide] amide

There total 7 articles about 5-benzyloxy-4(S)-methyl-2(R)-[2-(4-n-propylphenyl)ethyl]pentanoic acid 1-[(S)-tert-butylglycine phenylamide] 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: 65.0%

(S)-tert-butylglycine phenylamide (171764-05-9) + 5-benzyloxy-4(S)-methyl-2(R)-[2-(4-n-propylphenyl)ethyl]pentanoic acid (189217-63-8) → 5-benzyloxy-4(S)-methyl-2(R)-[2-(4-n-propylphenyl)ethyl]pentanoic acid 1-[(S)-tert-butylglycine phenylamide] amide (189217-66-1)

Guidance literature:

With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4020(99)00334-8

Reference yield:

4-(4-n-propylphenyl)butanoic acid (25711-53-9) → 5-benzyloxy-4(S)-methyl-2(R)-[2-(4-n-propylphenyl)ethyl]pentanoic acid 1-[(S)-tert-butylglycine phenylamide] amide (189217-66-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 75 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 20 °C

2.1: LDA / cyclohexane; tetrahydrofuran / 0.25 h / 20 °C

2.2: 65 percent / DMPU / cyclohexane; tetrahydrofuran / -82 - -20 °C

3.1: 62 percent / aq. HCl / tetrahydrofuran / 34 h / Heating

4.1: 65 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole hydrate / CH₂Cl₂ / 20 °C

With hydrogenchloride; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; cyclohexane; 1.1: Condensation / 2.1: Metallation / 2.2: Alkylation / 3.1: Hydrolysis / 4.1: Condensation;

DOI:10.1016/S0040-4020(99)00334-8

Reference yield:

(S)-3-benzyloxy-2-methylpropan-1-ol (63930-46-1) → 5-benzyloxy-4(S)-methyl-2(R)-[2-(4-n-propylphenyl)ethyl]pentanoic acid 1-[(S)-tert-butylglycine phenylamide] amide (189217-66-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 77 percent / NIS; Ph₃P / 1 h / 0 °C

2.1: LDA / cyclohexane; tetrahydrofuran / 0.25 h / 20 °C

2.2: 65 percent / DMPU / cyclohexane; tetrahydrofuran / -82 - -20 °C

3.1: 62 percent / aq. HCl / tetrahydrofuran / 34 h / Heating

4.1: 65 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole hydrate / CH₂Cl₂ / 20 °C

With hydrogenchloride; N-iodo-succinimide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; cyclohexane; 1.1: Substitution / 2.1: Metallation / 2.2: Alkylation / 3.1: Hydrolysis / 4.1: Condensation;

DOI:10.1016/S0040-4020(99)00334-8

upstream raw materials:

(S)-tert-butylglycine phenylamide

5-benzyloxy-4(S)-methyl-2(R)-[2-(4-n-propylphenyl)ethyl]pentanoic acid

4-(4-n-propylphenyl)butanoic acid

(S)-3-benzyloxy-2-methylpropan-1-ol

Downstream raw materials:

5-hydroxy-4(S)-methyl-2(R)-[2-(4-n-propylphenyl)ethyl]pentanoic acid 1-[(S)-tert-butylglycine phenylamide] amide

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