2-tert-butoxycarbonylamino-2-[5-(2-hydroxy-ethyl)-5-isopropyl-4-oxo-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester

Base Information

Chemical Name:2-tert-butoxycarbonylamino-2-[5-(2-hydroxy-ethyl)-5-isopropyl-4-oxo-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester
CAS No.:288404-51-3
Molecular Formula:C₂₄H₃₄N₂O₆
Molecular Weight:446.544
Hs Code.:

2-<i>tert</i>-butoxycarbonylamino-2-[5-(2-hydroxy-ethyl)-5-isopropyl-4-oxo-4,5-dihydro-1<i>H</i>-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester

Synonyms:2-tert-butoxycarbonylamino-2-[5-(2-hydroxy-ethyl)-5-isopropyl-4-oxo-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester

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Chemical Property of 2-tert-butoxycarbonylamino-2-[5-(2-hydroxy-ethyl)-5-isopropyl-4-oxo-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester

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Technology Process of 2-tert-butoxycarbonylamino-2-[5-(2-hydroxy-ethyl)-5-isopropyl-4-oxo-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester

There total 6 articles about 2-tert-butoxycarbonylamino-2-[5-(2-hydroxy-ethyl)-5-isopropyl-4-oxo-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic 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: 77.0%

: (S)-2-Benzyl-2-tert-butoxycarbonylamino-4-[(Z)-(R)-3-isopropyl-2-oxo-tetrahydro-furan-3-ylimino]-butyric acid methyl ester

: [3-benzyl-1-(3-isopropyl-2-oxo-tetrahydro-furan-3-yl)-2-oxo-2,3-dihydro-1H-pyrrol-3-yl]-carbamic acid tert-butyl ester

: 288404-51-3
2-tert-butoxycarbonylamino-2-[5-(2-hydroxy-ethyl)-5-isopropyl-4-oxo-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester

Guidance literature:: With 18-crown-6 ether; potassium hexamethylsilazane; at 0 - 20 ℃;
DOI:10.1021/ol0059293

Reference yield:

: 145452-08-0
(R)-2-Amino-2-isopropyl-5-methyl-hex-4-enoic acid methyl ester

: 288404-51-3
2-tert-butoxycarbonylamino-2-[5-(2-hydroxy-ethyl)-5-isopropyl-4-oxo-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 93 percent / i-Pr₂NEt / tetrahydrofuran / 4 h / 20 °C

2: 95 percent / O₃; PPh₃ / -78 °C

3: 78 percent / NaBH₃CN; aq. HCl / methanol / 3 h / 20 °C

4: 83 percent / H₂ / Pd(C) / ethanol / 1 h

5: toluene

6: 77 percent / KHMDS; 18-crown-6 / tetrahydrofuran / 3 h / 20 °C

With hydrogenchloride; 18-crown-6 ether; hydrogen; potassium hexamethylsilazane; sodium cyanoborohydride; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; toluene; 1: benzyloxycarbonylation / 2: Oxidation / 3: Reduction / 4: Hydrogenation / 5: Condensation / 6: Ring cleavage;
DOI:10.1021/ol0059293

Reference yield:

: 288404-44-4
((R)-3-Isopropyl-2-oxo-tetrahydro-furan-3-yl)-carbamic acid benzyl ester

: 288404-51-3
2-tert-butoxycarbonylamino-2-[5-(2-hydroxy-ethyl)-5-isopropyl-4-oxo-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 83 percent / H₂ / Pd(C) / ethanol / 1 h

2: toluene

3: 77 percent / KHMDS; 18-crown-6 / tetrahydrofuran / 3 h / 20 °C

With 18-crown-6 ether; hydrogen; potassium hexamethylsilazane; palladium on activated charcoal; In tetrahydrofuran; ethanol; toluene; 1: Hydrogenation / 2: Condensation / 3: Ring cleavage;
DOI:10.1021/ol0059293