(αS)-3,4-dioxo-2-(1-methylethoxy)-α-phenylmethyloxycarbonylamino-1-cyclobutene-1-butyric acid

Base Information

Chemical Name:(αS)-3,4-dioxo-2-(1-methylethoxy)-α-phenylmethyloxycarbonylamino-1-cyclobutene-1-butyric acid
CAS No.:253353-17-2
Molecular Formula:C₁₉H₂₁NO₇
Molecular Weight:375.378
Hs Code.:

Synonyms:(αS)-3,4-dioxo-2-(1-methylethoxy)-α-phenylmethyloxycarbonylamino-1-cyclobutene-1-butyric acid

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Chemical Property of (αS)-3,4-dioxo-2-(1-methylethoxy)-α-phenylmethyloxycarbonylamino-1-cyclobutene-1-butyric acid

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Technology Process of (αS)-3,4-dioxo-2-(1-methylethoxy)-α-phenylmethyloxycarbonylamino-1-cyclobutene-1-butyric acid

There total 3 articles about (αS)-3,4-dioxo-2-(1-methylethoxy)-α-phenylmethyloxycarbonylamino-1-cyclobutene-1-butyric acid 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: 80.0%

: 253353-16-1
1,1-dimethylethyl (αS)-γ-(1,1-dimethylethoxycarbonyl)-3,4-dioxo-2-(1-methylethoxy)-α-(phenylmethyloxycarbonylamino)-1-cyclobutene-1-butyrate

: 253353-17-2
(αS)-3,4-dioxo-2-(1-methylethoxy)-α-phenylmethyloxycarbonylamino-1-cyclobutene-1-butyric acid

Guidance literature:: 1,1-dimethylethyl (αS)-γ-(1,1-dimethylethoxycarbonyl)-3,4-dioxo-2-(1-methylethoxy)-α-(phenylmethyloxycarbonylamino)-1-cyclobutene-1-butyrate; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 12h;

With triethylamine; In dichloromethane; at 20 ℃; for 0.166667h; Further stages.;
DOI:10.1021/ol990286g

Reference yield:

: 253353-15-0
1,1-dimethylethyl (αS)-2,3-bis(1-methylethoxy)-γ-(1,1-dimethylethoxycarbonyl)-1-hydroxy-4-oxo-α-(phenylmethyloxycarbonylamino)-2-cyclobutene-1-butyrate

: 253353-17-2
(αS)-3,4-dioxo-2-(1-methylethoxy)-α-phenylmethyloxycarbonylamino-1-cyclobutene-1-butyric acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: 90 percent / aq. HCl / CH₂Cl₂ / 12 h / 20 °C

2.1: TFA / CH₂Cl₂ / 12 h / 20 °C

2.2: 80 percent / Et₃N / CH₂Cl₂ / 0.17 h / 20 °C

With hydrogenchloride; trifluoroacetic acid; In dichloromethane;
DOI:10.1021/ol990286g

Reference yield:

: 16881-41-7
di-tert-butyl N-Cbz-L-glutamate

: 253353-17-2
(αS)-3,4-dioxo-2-(1-methylethoxy)-α-phenylmethyloxycarbonylamino-1-cyclobutene-1-butyric acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: LHMDS; LiCl; DMPU / tetrahydrofuran / 2 h / -78 °C

1.2: 92 percent / tetrahydrofuran / 1 h / -45 °C

2.1: 90 percent / aq. HCl / CH₂Cl₂ / 12 h / 20 °C

3.1: TFA / CH₂Cl₂ / 12 h / 20 °C

3.2: 80 percent / Et₃N / CH₂Cl₂ / 0.17 h / 20 °C

With hydrogenchloride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; trifluoroacetic acid; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol990286g