Phosphorus pentachloride → 3-Carbamoyloxymethyl-7-(2-methanesulfonamidothiazol-4-yl)-acetamido-3-cephem-4-carboxylic acid

HRID 127097ノート

反応式

HRID 127097 の反応式
[CH3:1][S:2]([NH:5][C:6]1[S:7][CH:8]=[C:9]([CH2:11][C:12]([OH:14])=O)[N:10]=1)(=[O:4])=[O:3].[C:15]([O:18][CH2:19][C:20]1[CH2:21][S:22][C@@H:23]2C(N)C(=O)[N:24]2[C:25]=1[C:26]([OH:28])=[O:27])(=[O:17])[NH2:16].P(Cl)(Cl)(Cl)(Cl)Cl.C[Si]([CH2:43][C:44]([NH2:46])=[O:45])(C)C>>[C:15]([O:18][CH2:19][C:20]1[CH:21]([NH:46][C:44](=[O:45])[CH3:43])[S:22][C@@H:23]2[CH:11]([C:9]3[N:10]=[C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[S:7][CH:8]=3)[C:12](=[O:14])[N:24]2[C:25]=1[C:26]([OH:28])=[O:27])(=[O:17])[NH2:16]

参加物

5

反応物 4

HCID 24819Phosphorus pentachlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 31595752-(2-Methanesulfonamido-1,3-thiazol-4-yl)acetic acidHCID 127847593-Carbamoyloxymethyl-7-amino-3-cephem-4-carboxylic acid

生成物 1

HCID 1317121093-Carbamoyloxymethyl-7-(2-methanesulfonamidothiazol-4-yl)-acetamido-3-cephem-4-carboxylic acid収率 76.1%

実験手順

2-Methanesulfonamidothiazol-4-ylacetic acid (1.13 g.), 3-carbamoyloxymethyl-7-amino-3-cephem-4-carboxylic acid (1.37 g.), phosphorus pentachloride (2.08 g.) and trimethylsilylacetamide (4.58 g.) were treated in the similar manner to that of Example 12 to give 3-carbamoyloxymethyl-7-(2-methanesulfonamidothiazol-4-yl)-acetamido-3-cephem-4-carboxylic acid (1.79 g.)

出典と根拠

ORDレコード
ord-3e7bd264c207483e9db2c231d0436d0c
出典データセット
uspto-grants-1981_03
特許番号
US04254260

反応ノート

読み込み中…