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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
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HRID 2413447 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8857Ethyl Acetate2회HCID 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

생성물 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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 31374Dimethylacetamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-33cef257d50f4dd1bcb4a8e379714dc7
출처 데이터셋
uspto-grants-1985_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04496560

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