4-[(2S,3S)-3-Benzyl-4-oxo-1-((R)-1-phenyl-ethylcarbamoyl)-azetidin-2-yloxy]-benzoic acid

Base Information

Chemical Name:4-[(2S,3S)-3-Benzyl-4-oxo-1-((R)-1-phenyl-ethylcarbamoyl)-azetidin-2-yloxy]-benzoic acid
CAS No.:256409-65-1
Molecular Formula:C₂₆H₂₄N₂O₅
Molecular Weight:444.487
Hs Code.:

Synonyms:4-[(2S,3S)-3-Benzyl-4-oxo-1-((R)-1-phenyl-ethylcarbamoyl)-azetidin-2-yloxy]-benzoic acid

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Chemical Property of 4-[(2S,3S)-3-Benzyl-4-oxo-1-((R)-1-phenyl-ethylcarbamoyl)-azetidin-2-yloxy]-benzoic acid

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Technology Process of 4-[(2S,3S)-3-Benzyl-4-oxo-1-((R)-1-phenyl-ethylcarbamoyl)-azetidin-2-yloxy]-benzoic acid

There total 9 articles about 4-[(2S,3S)-3-Benzyl-4-oxo-1-((R)-1-phenyl-ethylcarbamoyl)-azetidin-2-yloxy]-benzoic 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: 90.0%

: 256409-76-4
(3S,4S)-3-benzyl-4-[4-(1,1-diphenylmethoxycarbonyl)phenoxy]-1-[(R)-1-(phenylethyl)aminocarbonyl]azetidin-2-one

: 256409-65-1
4-[(2S,3S)-3-Benzyl-4-oxo-1-((R)-1-phenyl-ethylcarbamoyl)-azetidin-2-yloxy]-benzoic acid

Guidance literature:: With methoxybenzene; trifluoroacetic acid; at 5 ℃; for 1.5h;
DOI:10.1016/S0968-0896(01)00209-7

Reference yield:

: 33375-06-3
(1R)-1-phenylethyl isocyanate

: 256409-65-1
4-[(2S,3S)-3-Benzyl-4-oxo-1-((R)-1-phenyl-ethylcarbamoyl)-azetidin-2-yloxy]-benzoic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 83 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / 20 °C

2: 90 percent / trifluoroacetic acid; anisole / 1.5 h / 5 °C

With dmap; methoxybenzene; triethylamine; trifluoroacetic acid; In dichloromethane;
DOI:10.1016/S0968-0896(01)00209-7

Reference yield:

: 100-39-0
benzyl bromide

: 256409-65-1
4-[(2S,3S)-3-Benzyl-4-oxo-1-((R)-1-phenyl-ethylcarbamoyl)-azetidin-2-yloxy]-benzoic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: LDA / tetrahydrofuran; heptane; ethylbenzene / 0.33 h / -55 °C

1.2: 98 percent / tetrahydrofuran; heptane; ethylbenzene / 1.5 h / -40 - -15 °C

2.1: dimethylformamide; acetic acid / 0.67 h / 50 - 55 °C

3.1: 53 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 25 °C

4.1: 74 percent / aq. NaOH / acetone / 3 h / 10 - 15 °C

5.1: 83 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / 20 °C

6.1: 90 percent / trifluoroacetic acid; anisole / 1.5 h / 5 °C

With dmap; sodium hydroxide; tetrabutyl ammonium fluoride; methoxybenzene; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; dichloromethane; ethylbenzene; acetic acid; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0968-0896(01)00209-7