참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | 4-Methylmorpholine | HCID 7972 | — |
| 반응물 | Phosphorodichloridic acid, phenyl ester | HCID 13038 | — |
| 반응물 | (4-Methoxyphenyl)methyl (6R,7R)-3-(chloromethyl)-8-oxo-7-((2-phenylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate | HCID 10874591 | — |
| 반응물 | 2-(2-t-Butoxycarbonylamino-4-thiazolyl)-2-(1-diphenylmethoxycarbonyl-1-methylethoxyimino)acetic acid | HCID 54272829 | — |
| 용매 | Dichloromethane | HCID 6344 | — |
| 용매 | Ethyl Acetate | HCID 8857 | — |
| 생성물 | HCID 131717475 | HCID 131717475 | 83.1% |
반응 단계
To a suspension of 7β-amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (1) p-toluenesulfonate (2.705 g: 5 mMol.) in dichloromethane (50 ml) are added N-methylmorpholin (0.55 ml; 1 Eq.) and 2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-(1-diphenylmethoxycarbonyl-1-methylethoxyimino)acetic acid (3.51 g; 1.3 Eq.) at 0° C. and then phenylphosphoric dichloride (0.97 ml; 1.3 Eq.) and N-methylmorpholin (1.65 ml; 3 Eq.) at -40° C., and the mixture is stirred at -40° to -10° C. for 1.5 hours. The reaction mixture is diluted with ethyl acetate, washed with water, diluted hydrochloric acid and water, dried, and concentrated under reduced pressure. The residue is purified by silica gel chromatography (toluene:ethyl acetate) to give 7β-[2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-(1-diphenylmethoxycarbonyl-1-methylethoxyimino)acetamido]-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (2) (3.70 g).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US05134138 |
|---|
| 출처 데이터셋 | uspto-grants-1992_07 |
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| ORD ID | ord-a3d248e291de4d8d9313a6d8c07afc6e |
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| 출처 메모 | uspto-grants-1992_07 |
|---|
