benzyl N-{cis-(2R)-2-[2-acetylamino-cyclopropyloxy]-propionyl}-L-alanyl-D-isoglutaminate

Base Information

Chemical Name:benzyl N-{cis-(2R)-2-[2-acetylamino-cyclopropyloxy]-propionyl}-L-alanyl-D-isoglutaminate
CAS No.:682749-82-2
Molecular Formula:C₂₃H₃₂N₄O₇
Molecular Weight:476.53
Hs Code.:

Synonyms:benzyl N-{cis-(2R)-2-[2-acetylamino-cyclopropyloxy]-propionyl}-L-alanyl-D-isoglutaminate

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Chemical Property of benzyl N-{cis-(2R)-2-[2-acetylamino-cyclopropyloxy]-propionyl}-L-alanyl-D-isoglutaminate

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Technology Process of benzyl N-{cis-(2R)-2-[2-acetylamino-cyclopropyloxy]-propionyl}-L-alanyl-D-isoglutaminate

There total 15 articles about benzyl N-{cis-(2R)-2-[2-acetylamino-cyclopropyloxy]-propionyl}-L-alanyl-D-isoglutaminate 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%

: 75-36-5
acetyl chloride

: 682749-76-4
benzyl N-{cis-(2R)-2-[2-(tert-butoxycarbonylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate

: 682749-82-2
benzyl N-{cis-(2R)-2-[2-acetylamino-cyclopropyloxy]-propionyl}-L-alanyl-D-isoglutaminate

Guidance literature:: benzyl N-{cis-(2R)-2-[2-(tert-butoxycarbonylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate; With hydrogenchloride; In ethyl acetate; at 20 ℃; for 3h;

acetyl chloride; With triethylamine; In dichloromethane; at 20 ℃; for 14h; Further stages.;
DOI:10.1016/j.tet.2004.01.036

Reference yield:

: 75-36-5
acetyl chloride

: 682749-76-4
benzyl N-{trans-(2R)-2-[2-(tert-butoxycarbonylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate

: 682749-82-2
benzyl N-{trans-(2R)-2-[2-acetylamino-cyclopropyloxy]-propionyl}-L-alanyl-D-isoglutaminate

Guidance literature:: benzyl N-{trans-(2R)-2-[2-(tert-butoxycarbonylamino)cyclopropyloxy]propionyl}-L-alanyl-D-isoglutaminate; With hydrogenchloride; In ethyl acetate; at 20 ℃; for 3h;

acetyl chloride; With triethylamine; In dichloromethane; at 20 ℃; for 14h; Further stages.;
DOI:10.1016/j.tet.2004.01.036

Reference yield:

: 682749-65-1
isobutyl (2R)-2-(vinyloxy)propanoate

: 682749-82-2
benzyl N-{trans-(2R)-2-[2-acetylamino-cyclopropyloxy]-propionyl}-L-alanyl-D-isoglutaminate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 27 percent / [(Rh(OAc)2)2] / CH₂Cl₂ / 8 h / 20 °C

2.1: CF₃COOH / CH₂Cl₂ / 18 h

3.1: 20 percent / Et₃N; diphenylphosphorylazide / 2 h / 70 °C

4.1: KOH; ethanol / 2 h / 20 °C

5.1: isobutyl chloroformate; N-methyl-morpholine / ethyl acetate; dimethylformamide / 0.08 h / -15 °C

5.2: 11 percent / N-methyl-morpholine / ethyl acetate; dimethylformamide / 18 h / 20 °C

6.1: hydrochloric acid / ethyl acetate / 3 h / 20 °C

6.2: Et₃N / CH₂Cl₂ / 14 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; dirhodium tetraacetate; potassium hydroxide; ethanol; diphenylphosphoranyl azide; triethylamine; trifluoroacetic acid; isobutyl chloroformate; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.01.036