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

HRID 325478
ノート
印刷プレビュー

反応式

HRID 325478 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 1N-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) give 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-c3bc920823a240a28a7baa9f985c0d62
出典データセット
uspto-grants-1984_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04440683

反応ノート

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