Acetic acid (6R,7R)-2-chlorocarbonyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester

Base Information

Chemical Name:Acetic acid (6R,7R)-2-chlorocarbonyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester
CAS No.:347193-74-2
Molecular Formula:C₁₈H₁₇ClN₂O₅S
Molecular Weight:408.862
Hs Code.:

Synonyms:Acetic acid (6R,7R)-2-chlorocarbonyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester

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Chemical Property of Acetic acid (6R,7R)-2-chlorocarbonyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester

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Technology Process of Acetic acid (6R,7R)-2-chlorocarbonyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester

There total 1 articles about Acetic acid (6R,7R)-2-chlorocarbonyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl 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:

: 859-07-4
cephaloram

: 347193-74-2
Acetic acid (6R,7R)-2-chlorocarbonyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester

Guidance literature:: With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/S0223-5234(01)01211-9

Reference yield:

: 347193-74-2
Acetic acid (6R,7R)-2-chlorocarbonyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester

: 347193-75-3
N-((6R)-3-acetoxymethyl-2-hydroxymethyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-7t-yl)-2-phenyl-acetamide

Guidance literature:: With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; at 0 ℃; for 0.5h;
DOI:10.1016/S0223-5234(01)01211-9

Reference yield:

: 347193-74-2
Acetic acid (6R,7R)-2-chlorocarbonyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester

: 4-Fluoro-benzoic acid (6R,7S)-3-acetoxymethyl-7-methoxy-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-en-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 1.7 g / LiAl(t-BuO)3H / tetrahydrofuran / 0.5 h / 0 °C

2: 70 percent / 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide*HCl; 2,6-dimethylaminopyridine / CH₂Cl₂ / 3 h / 0 °C

3: 2,6-dimethylaminopyridine; Et₃N / CH₂Cl₂ / 1 h / 20 °C

4: N,N-diethylethylenediamine / CH₂Cl₂ / 48 h / 20 °C

5: TFA / CH₂Cl₂ / 0.33 h / 20 °C

6: NaNO₂; H₂SO₄ / H₂O; CH₂Cl₂ / 1 h / 0 °C

7: Rh₂OAc₄ / CH₂Cl₂ / 1.5 h / 0 °C

8: MCPBA; NaHCO₃ / CH₂Cl₂ / 2 h / 0 °C

With sulfuric acid; N,N'-dimethylpyridine-2,6-diamine; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium tri-t-butoxyaluminum hydride; triethylamine; N,N-diethylethylenediamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; sodium nitrite; dirhodium tetraacetate; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/S0223-5234(01)01211-9