2-[1-(2-Amino-thiazol-4-yl)-1-((2S,3S)-2-{[2-(3,4-dihydroxy-benzoylamino)-ethylcarbamoyl]-methyl}-4-oxo-1-sulfo-azetidin-3-ylcarbamoyl)-meth-(Z)-ylideneaminooxy]-2-methyl-propionic acid

Base Information

Chemical Name:2-[1-(2-Amino-thiazol-4-yl)-1-((2S,3S)-2-{[2-(3,4-dihydroxy-benzoylamino)-ethylcarbamoyl]-methyl}-4-oxo-1-sulfo-azetidin-3-ylcarbamoyl)-meth-(Z)-ylideneaminooxy]-2-methyl-propionic acid
CAS No.:141993-01-3
Molecular Formula:C₂₃H₂₇N₇O₁₂S₂
Molecular Weight:657.639
Hs Code.:

2-[1-(2-Amino-thiazol-4-yl)-1-((2S,3S)-2-{[2-(3,4-dihydroxy-benzoylamino)-ethylcarbamoyl]-methyl}-4-oxo-1-sulfo-azetidin-3-ylcarbamoyl)-meth-(Z)-ylideneaminooxy]-2-methyl-propionic acid

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Chemical Property of 2-[1-(2-Amino-thiazol-4-yl)-1-((2S,3S)-2-{[2-(3,4-dihydroxy-benzoylamino)-ethylcarbamoyl]-methyl}-4-oxo-1-sulfo-azetidin-3-ylcarbamoyl)-meth-(Z)-ylideneaminooxy]-2-methyl-propionic acid

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Technology Process of 2-[1-(2-Amino-thiazol-4-yl)-1-((2S,3S)-2-{[2-(3,4-dihydroxy-benzoylamino)-ethylcarbamoyl]-methyl}-4-oxo-1-sulfo-azetidin-3-ylcarbamoyl)-meth-(Z)-ylideneaminooxy]-2-methyl-propionic acid

There total 10 articles about 2-[1-(2-Amino-thiazol-4-yl)-1-((2S,3S)-2-{[2-(3,4-dihydroxy-benzoylamino)-ethylcarbamoyl]-methyl}-4-oxo-1-sulfo-azetidin-3-ylcarbamoyl)-meth-(Z)-ylideneaminooxy]-2-methyl-propionic 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:

: 142488-27-5
Potassium; (2S,3S)-3-benzyloxycarbonylamino-2-benzyloxycarbonylmethyl-4-oxo-azetidine-1-sulfonate

: 141993-01-3
2-[1-(2-Amino-thiazol-4-yl)-1-((2S,3S)-2-{[2-(3,4-dihydroxy-benzoylamino)-ethylcarbamoyl]-methyl}-4-oxo-1-sulfo-azetidin-3-ylcarbamoyl)-meth-(Z)-ylideneaminooxy]-2-methyl-propionic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 64 percent / H₂ / 10percent Pd/C / dimethylformamide / 1.5 h / Ambient temperature

2: 1.) BSA / 1.) CH₂Cl₂, RT, 1 h, 2.) CH₂Cl₂, a) -45 deg C, 15 min, b) RT, 1 h

3: Et₃N / CH₂Cl₂ / 0.33 h / -80 °C

4: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

5: TFA

6: H₂O / methanol / 2 h / pH 8

With benzenesulfonamide; water; hydrogen; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0223-5234(92)90101-6

Reference yield:

: 2-[1-(2-Amino-thiazol-4-yl)-1-((2S,3S)-2-{[2-(3,4-diacetoxy-benzoylamino)-ethylcarbamoyl]-methyl}-4-oxo-1-sulfo-azetidin-3-ylcarbamoyl)-meth-(Z)-ylideneaminooxy]-2-methyl-propionic acid

: 141993-01-3
2-[1-(2-Amino-thiazol-4-yl)-1-((2S,3S)-2-{[2-(3,4-dihydroxy-benzoylamino)-ethylcarbamoyl]-methyl}-4-oxo-1-sulfo-azetidin-3-ylcarbamoyl)-meth-(Z)-ylideneaminooxy]-2-methyl-propionic acid

Guidance literature:: With water; In methanol; for 2h; Yield given; pH 8;
DOI:10.1016/0223-5234(92)90101-6

Reference yield:

: 57929-25-6
3,4-(diacetyloxy)benzoyl chloride

: 141993-01-3
2-[1-(2-Amino-thiazol-4-yl)-1-((2S,3S)-2-{[2-(3,4-dihydroxy-benzoylamino)-ethylcarbamoyl]-methyl}-4-oxo-1-sulfo-azetidin-3-ylcarbamoyl)-meth-(Z)-ylideneaminooxy]-2-methyl-propionic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 71 percent / Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

2: 96 percent / aq. TFA / 0.5 h / Ambient temperature

3: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

4: TFA

5: H₂O / methanol / 2 h / pH 8

With water; triethylamine; trifluoroacetic acid; In methanol; dichloromethane;
DOI:10.1016/0223-5234(92)90101-6