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Sodium Iodide → Phthalid-3-yl 7-[2-(2-aminothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylate

HRID 1088134
ノート
印刷プレビュー

反応式

HRID 1088134 の反応式
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([NH:10][CH:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([OH:22])=[O:21])=[C:15]([CH:18]=[CH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C(N(CC)CC)C.Br[CH:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:35](=[O:36])[O:34]1.[I-].[Na+]>CN(C)C=O.O.C(OCC)(=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([NH:10][CH:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([O:22][CH:33]4[C:42]5[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=5)[C:35](=[O:36])[O:34]4)=[O:21])=[C:15]([CH:18]=[CH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 962181(3H)-Isobenzofuranone, 3-bromo-HCID 88469260Unii-nyh6qmq9H0

生成物 1

HCID 88469456Phthalid-3-yl 7-[2-(2-aminothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylate収率 55.1%

試薬・触媒・溶媒 3

HCID 962
Water
溶媒
HCID 6228Dimethylformamide溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 7-[2-(2-aminothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylic acid (2.0 g) in N,N-dimethylformamide (15 ml) were added triethylamine (0.55 g), 3-bromophthalide (1.2 g) and sodium iodide (0.82 g) in turn in a stream of nitrogen, and the mixture was stirred at ambient temperature for half an hour. After the reaction mixture was poured into a mixture of ethyl acetate (300 ml) and water (200 ml), the organic layer was separated out, washed with water and a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate, followed by treating with charcoal. After the filtrate was concentrated and thereto was added diethyl ether. The precipitated substance was collected by filtration to obtain phthalid-3-yl 7-[2-(2-aminothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylate (1.5 g).

後処理

  1. customthe organic layer was separated out
  2. washwashed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate
  4. additionby treating with charcoal
  5. concentrationAfter the filtrate was concentrated
  6. additionwas added diethyl ether
  7. filtrationThe precipitated substance was collected by filtration

出典と根拠

ORDレコード
ord-d09274dd3a8345929e5450c243de98d3
出典データセット
uspto-grants-1990_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04960889

反応ノート

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