3-tert-butoxycarbonylamino-4-(4-tert-butoxy-phenyl)-butyric acid methyl ester

Base Information

• Chemical Name: 3-tert-butoxycarbonylamino-4-(4-tert-butoxy-phenyl)-butyric acid methyl ester
• CAS No.: 565430-82-2
• Molecular Formula: C₂₀H₃₁NO₅
• Molecular Weight: 365.47
• Mol file: 565430-82-2.mol

Synonyms:3-tert-butoxycarbonylamino-4-(4-tert-butoxy-phenyl)-butyric acid methyl ester

Chemical Property of 3-tert-butoxycarbonylamino-4-(4-tert-butoxy-phenyl)-butyric acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 3-tert-butoxycarbonylamino-4-(4-tert-butoxy-phenyl)-butyric acid methyl ester

There total 1 articles about 3-tert-butoxycarbonylamino-4-(4-tert-butoxy-phenyl)-butyric 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:

Boc-D-Tyr(t-Bu)-OH (507276-74-6) → 3-tert-butoxycarbonylamino-4-(4-tert-butoxy-phenyl)-butyric acid methyl ester (565430-82-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: isobutylchloroformate; N-methylmorpholine / tetrahydrofuran / 0.33 h / -20 °C

1.2: tetrahydrofuran; diethyl ether / 0.5 h / -20 °C

2.1: PhCO₂Ag; NEt₃ / 1.25 h

With 4-methyl-morpholine; silver benzoate; triethylamine; isobutyl chloroformate; In tetrahydrofuran; 1.2: Arndt-Eistert homologation;

DOI:10.1021/ol027237f

Reference yield:

3-tert-butoxycarbonylamino-4-(4-tert-butoxy-phenyl)-butyric acid methyl ester (565430-82-2) → [1-(4-tert-butoxy-benzyl)-3-oxo-propyl]-carbamic acid tert-butyl ester (565430-83-3)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃; for 1h;

DOI:10.1021/ol027237f

Reference yield:

3-tert-butoxycarbonylamino-4-(4-tert-butoxy-phenyl)-butyric acid methyl ester (565430-82-2) → 2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,6-dihydroxy-non-4-enoic acid

Guidance literature:

Multi-step reaction with 4 steps

1: DIBAL-H / toluene / 1 h / -78 °C

2: tetrahydrofuran / 1.5 h / -78 - -40 °C

3: 51 percent / Cl₂(PCy)3(IMesH₂)RuCHPh / CH₂Cl₂ / 4 h / Heating

4: 69 percent / LiOH; H₂O₂ / tetrahydrofuran; H₂O / 3 h / 20 °C

With lithium hydroxide; dihydrogen peroxide; diisobutylaluminium hydride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; water; toluene;

DOI:10.1021/ol027237f

upstream raw materials:

Boc-D-Tyr(t-Bu)-OH

Downstream raw materials:

[1-(4-tert-butoxy-benzyl)-3-oxo-propyl]-carbamic acid tert-butyl ester