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

Base Information

Chemical Name:4-Fluoro-benzoic acid (6R,7S)-3-acetoxymethyl-7-methoxy-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-2-ylmethyl ester
CAS No.:347193-90-2
Molecular Formula:C₁₈H₁₈FNO₆S
Molecular Weight:395.408
Hs Code.:

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

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

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

There total 7 articles about 4-Fluoro-benzoic acid (6R,7S)-3-acetoxymethyl-7-methoxy-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-2-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

: 347193-90-2
4-Fluoro-benzoic acid (6R,7S)-3-acetoxymethyl-7-methoxy-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: oxalyl chloride; DMF / CH₂Cl₂ / 1 h / 0 °C

2: 1.7 g / LiAl(t-BuO)3H / tetrahydrofuran / 0.5 h / 0 °C

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

4: 2,6-dimethylaminopyridine; Et₃N / CH₂Cl₂ / 1 h / 20 °C

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

6: TFA / CH₂Cl₂ / 0.33 h / 20 °C

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

8: Rh₂OAc₄ / CH₂Cl₂ / 1.5 h / 0 °C

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

Reference yield:

: 347193-88-8
(6R)-3-acetoxymethyl-2-(4-fluorobenzoyl)oxymethyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-7t-amine

: 347193-90-2
4-Fluoro-benzoic acid (6R,7S)-3-acetoxymethyl-7-methoxy-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 2 steps

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

2: Rh₂OAc₄ / CH₂Cl₂ / 1.5 h / 0 °C

With sulfuric acid; sodium nitrite; dirhodium tetraacetate; In dichloromethane; water;
DOI:10.1016/S0223-5234(01)01211-9

Reference yield:

: 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

: 347193-90-2
4-Fluoro-benzoic acid (6R,7S)-3-acetoxymethyl-7-methoxy-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

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

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

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

4: TFA / CH₂Cl₂ / 0.33 h / 20 °C

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

6: Rh₂OAc₄ / CH₂Cl₂ / 1.5 h / 0 °C

With sulfuric acid; N,N'-dimethylpyridine-2,6-diamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N,N-diethylethylenediamine; trifluoroacetic acid; sodium nitrite; dirhodium tetraacetate; In dichloromethane; water;
DOI:10.1016/S0223-5234(01)01211-9