(S)-2-tert-Butoxycarbonylamino-3-cyclohexyl-propionic acid ethyl ester

Base Information

• Chemical Name: (S)-2-tert-Butoxycarbonylamino-3-cyclohexyl-propionic acid ethyl ester
• CAS No.: 169512-90-7
• Molecular Formula: C₁₆H₂₉NO₄
• Molecular Weight: 299.411
• Mol file: 169512-90-7.mol

Synonyms:(S)-2-tert-Butoxycarbonylamino-3-cyclohexyl-propionic acid ethyl ester

Chemical Property of (S)-2-tert-Butoxycarbonylamino-3-cyclohexyl-propionic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of (S)-2-tert-Butoxycarbonylamino-3-cyclohexyl-propionic acid ethyl ester

There total 1 articles about (S)-2-tert-Butoxycarbonylamino-3-cyclohexyl-propionic acid ethyl 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: 95.0%

ethyl N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalaninate (4522-04-7,53588-99-1) → (S)-2-tert-Butoxycarbonylamino-3-cyclohexyl-propionic acid ethyl ester (169512-90-7)

Guidance literature:

With hydrogen; platinum(IV) oxide;

DOI:10.1016/S0040-4039(00)95215-8

Reference yield: 95.0%

dimethyl lithiomethylphosphonate (34939-91-8,58648-56-9) + (S)-2-tert-Butoxycarbonylamino-3-cyclohexyl-propionic acid ethyl ester (169512-90-7) → ((S)-3-tert-Butoxycarbonylamino-4-cyclohexyl-2-oxo-butyl)-phosphonic acid dimethyl ester (124032-37-7)

Guidance literature:

In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)95215-8

Reference yield:

(S)-2-tert-Butoxycarbonylamino-3-cyclohexyl-propionic acid ethyl ester (169512-90-7) → (2S,4S,5S)-5-amino-6-cyclohexyl-4-hydroxy-2-isopropyl hexanoic acid n-butyl amide (105852-64-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 95 percent / tetrahydrofuran

2: 88 percent / n-BuLi / tetrahydrofuran; hexane / 1 h at -10 deg C, 1.5 h at room temp.

3: NaBH₄ / methanol / -30 °C

4: DBU / dimethylformamide / 90 °C

5: 93 percent / H₂ / 10percent Pd/C

6: DBU / dimethylformamide / 90 °C

7: 60 percent / Al(CH₃)3 / CH₂Cl₂ / 3 h / Heating

8: TFA / CH₂Cl₂ / 0 °C

With sodium tetrahydroborate; n-butyllithium; hydrogen; trimethylaluminum; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)95215-8

upstream raw materials:

ethyl N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalaninate

Downstream raw materials:

((S)-3-tert-Butoxycarbonylamino-4-cyclohexyl-2-oxo-butyl)-phosphonic acid dimethyl ester

(2S,4S,5S)-5-amino-6-cyclohexyl-4-hydroxy-2-isopropyl hexanoic acid n-butyl amide

((S)-1-Cyclohexylmethyl-4-methyl-2-oxo-pent-3-enyl)-carbamic acid tert-butyl ester

((E)-(S)-1-Cyclohexylmethyl-5-methyl-2-oxo-hex-3-enyl)-carbamic acid tert-butyl ester