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Ethyl Acetate → 2-Benzhydryloxycarbonyl-7-(3,4-dichlorophenylthio)-acetamido-3-(2-nicotinoylamino-thiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

HRID 2413447
ノート
印刷プレビュー

反応式

HRID 2413447 の反応式
Cl[C:2]1[CH:3]=[C:4]([CH2:9][C:10](Cl)=S)[CH:5]=[CH:6][C:7]=1Cl.[C:13]([Cl:18])(=O)[C:14]([Cl:16])=O.N[CH:20]1[C:27](=[O:28])[N:26]2[CH:21]1[S:22][CH2:23][C:24]([C:45]1[S:49][C:48]([NH:50][C:51](=[O:58])[C:52]3[CH:57]=[CH:56][CH:55]=[N:54][CH:53]=3)=[N:47][CH:46]=1)=[C:25]2C(OC(C1C=CC=CC=1)C1C=CC=CC=1)=O.[C:59]([O:62]CC)(=[O:61])[CH3:60]>C(OCC)C.CN(C)C(=O)C>[CH:9]([O:62][C:59]([CH2:60][C:27]([NH:26][C:25]1[N:26]2[CH:21]([S:22][CH2:23][C:24]=1[C:45]1[S:49][C:48]([NH:50][C:51](=[O:58])[C:52]3[CH:57]=[CH:56][CH:55]=[N:54][CH:53]=3)=[N:47][CH:46]=1)[CH:20]([S:49][C:45]1[CH:24]=[CH:23][C:14]([Cl:16])=[C:13]([Cl:18])[CH:46]=1)[C:27]2=[O:28])=[O:28])=[O:61])([C:4]1[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=1)[C:10]1[CH:55]=[CH:56][CH:57]=[CH:52][CH:51]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8857Ethyl Acetate2 回HCID 65578Oxalyl chlorideHCID 202763043,4-Dichlorophenylthioacetyl chlorideHCID 204304287-Amino-2-benzhydryloxycarbonyl-3-(2-nicotinoylamino-thiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

生成物 1

HCID 867399042-Benzhydryloxycarbonyl-7-(3,4-dichlorophenylthio)-acetamido-3-(2-nicotinoylamino-thiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 31374Dimethylacetamide溶媒

実験手順

A solution of 3,4-dichlorophenylthioacetyl chloride (prepared by the action of oxalyl chloride (8.4 cc) on the corresponding acid (3.99 g) in ethyl ether (48 cc), and replacement of the solvent) in ethyl acetate (20 cc) is added, in 10 minutes, to a solution of 7-amino-2-benzhydryloxycarbonyl-3-(2-nicotinoylamino-thiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (6.43 g) in N,N-dimethylacetamide (25 cc) at 0° C. After 1 hour at 0° C. followed by 40 minutes at a temperature of between 0 ° and 20° C., the reaction mixture is poured into ethyl acetate (250 cc) and this mixture is washed with distilled water (3×100 cc) and then with a saturated sodium chloride solution (100 cc). The organic phase is dried and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue is filtered on a column of silica (0.02-0.5 mm) (40 g), elution being carried out with a mixture (2 liters) of methylene chloride and methanol (95:5 by volume). The residue obtained after concentrating to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C. is crystallised from methylene chloride (20 cc) to give 2-benzhydryloxycarbonyl-7-(3,4-dichlorophenylthio)-acetamido-3-(2-nicotinoylamino-thiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (2.9 g) in the form of a pale yellow crystalline solid.

後処理

  1. washthis mixture is washed with distilled water (3×100 cc)
  2. customThe organic phase is dried
  3. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  4. filtrationThe residue is filtered on a column of silica (0.02-0.5 mm) (40 g), elution
  5. customThe residue obtained
  6. concentrationafter concentrating to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C.
  7. customis crystallised from methylene chloride (20 cc)

出典と根拠

ORDレコード
ord-33cef257d50f4dd1bcb4a8e379714dc7
出典データセット
uspto-grants-1985_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04496560

反応ノート

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