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Hydrochloric Acid → Diphenylmethyl 7-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylate

HRID 67852
ノート
印刷プレビュー

反応式

HRID 67852 の反応式
[O:1]([CH2:8][C:9]1[S:15][CH:14]2[CH:11]([C:12](=[O:37])[N:13]2[C:16](=[C:33]([OH:36])[CH2:34]Cl)[C:17]([O:19][CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C[OH:40]>O1CCCC1>[O:1]([CH2:8][C:9]([NH:10][CH:11]1[C:12](=[O:37])[N:13]2[C:16]([C:17]([O:19][CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])=[C:33]([OH:36])[CH2:34][S:15][C@H:14]12)=[O:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 70504488Diphenylmethyl alpha-[3-phenoxymethyl-7-oxo-2,6-diaza-4-thiabicyclo[3,2,0]hept-2-en-6-yl]-alpha-(2-chloro-1-hydroxyethylidene)acetate

生成物 1

HCID 67789034Diphenylmethyl 7-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To an ice cooled solution of diphenylmethyl α-[3-phenoxymethyl-7-oxo-2,6-diaza-4-thiabicyclo[3,2,0]hept-2-en-6-yl]-α-(2-chloro-1-hydroxyethylidene)acetate (36 mg) in a mixture of methanol and tetrahydrofuran (1:1) (1.1 ml) is added 1 N-hydrochloric acid (0.39 ml), warmed to the room temperature, and the mixture is stirred for 1.5 hours. The reaction mixture is poured into ice water, and is extracted with methylene chloride. The extract solution is washed with 5% aqueous sodium hydrogen carbonate solution and water, dried over sodium sulfate, and evaporated. Purification of the obtained residue by thin-layer chromatography using a mixture of benzene and ethyl acetate (3:2) gives diphenylmethyl 7-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylate (6 mg). m.p. 125°-126° C.

後処理

  1. extractionis extracted with methylene chloride
  2. washThe extract solution is washed with 5% aqueous sodium hydrogen carbonate solution and water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customPurification of the obtained residue by thin-layer chromatography
  6. additiona mixture of benzene and ethyl acetate (3:2)

出典と根拠

ORDレコード
ord-467bcea643b04317a19c32520eeab407
出典データセット
uspto-grants-1982_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04346218

反応ノート

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