2-benzyl-4-tert-butoxycarbonylamino-5-phenyl-pentanoic acid methyl ester

Base Information

• Chemical Name: 2-benzyl-4-tert-butoxycarbonylamino-5-phenyl-pentanoic acid methyl ester
• CAS No.: 194599-07-0
• Molecular Formula: C₂₄H₃₁NO₄
• Molecular Weight: 397.514

Synonyms:2-benzyl-4-tert-butoxycarbonylamino-5-phenyl-pentanoic acid methyl ester

Chemical Property of 2-benzyl-4-tert-butoxycarbonylamino-5-phenyl-pentanoic acid methyl ester

Chemical Property:

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Technology Process of 2-benzyl-4-tert-butoxycarbonylamino-5-phenyl-pentanoic acid methyl ester

There total 2 articles about 2-benzyl-4-tert-butoxycarbonylamino-5-phenyl-pentanoic acid 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: 100.0%

(E)-(S)-2-Benzyl-4-tert-butoxycarbonylamino-5-phenyl-pent-2-enoic acid methyl ester (819804-85-8) → 2-benzyl-4-tert-butoxycarbonylamino-5-phenyl-pentanoic acid methyl ester (194599-07-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; under 760 Torr;

DOI:10.1016/j.bmcl.2004.10.029

Reference yield:

Boc-L-phenylalaninal (72155-45-4) → 2-benzyl-4-tert-butoxycarbonylamino-5-phenyl-pentanoic acid methyl ester (194599-07-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / CHCl₃ / 20 °C

2: 100 percent / H₂ / Pd/C / methanol / 760 Torr

With hydrogen; palladium on activated charcoal; In methanol; chloroform; 1: Wittig reaction;

DOI:10.1016/j.bmcl.2004.10.029

Reference yield:

2-benzyl-4-tert-butoxycarbonylamino-5-phenyl-pentanoic acid methyl ester (194599-07-0) → {4-[(2R,4S)-5-((3S,5R)-3,5-Dibenzyl-2-oxo-pyrrolidin-1-yl)-4-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-pentyl]-phenoxy}-acetic acid (852460-16-3)

Guidance literature:

Multi-step reaction with 7 steps

1: TFA / CH₂Cl₂

2: K₂CO₃ / methanol

3: 85 percent / P₄-phosphazene / tetrahydrofuran / -20 °C

4: 93 percent / aq. HCl / propan-2-ol / 20 °C

5: 92 percent / H₂ / Pd(OH)2/C / ethanol

6: 64 percent / Cs₂CO₃ / dioxane / 80 °C

7: 39 percent / aq. TEA / tetrahydrofuran / Heating

With hydrogenchloride; P₄-phosphazene; TEA; hydrogen; potassium carbonate; caesium carbonate; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; isopropyl alcohol;

DOI:10.1016/j.bmcl.2004.10.029

upstream raw materials:

(E)-(S)-2-Benzyl-4-tert-butoxycarbonylamino-5-phenyl-pent-2-enoic acid methyl ester

Boc-L-phenylalaninal

Downstream raw materials:

(3S,5R)-3,5-Dibenzyl-pyrrolidin-2-one

{4-[(2R,4S)-5-((3S,5R)-3,5-Dibenzyl-2-oxo-pyrrolidin-1-yl)-4-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-pentyl]-phenoxy}-acetic acid

{4-[(2R,4S)-5-((3S,5R)-3,5-Dibenzyl-2-oxo-pyrrolidin-1-yl)-4-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-pentyl]-phenoxy}-acetic acid methyl ester

(3S,5R)-3,5-Dibenzyl-1-[(2S,4R)-4-(4-benzyloxy-benzyl)-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-hydroxy-5-oxo-pentyl]-pyrrolidin-2-one

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