Hydrochloric Acid → N-(m-iodobenzoyl)-1,3,4,6-tetra-O-acetyl-D-glucosamine

HRID 1086976ノート

反応式

HRID 1086976 の反応式
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.S(Cl)(Cl)=O.[C:15]([O:18][CH:19]1[O:33][C@H:32]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[C@@H:27]([O:28][C:29](=[O:31])[CH3:30])[C@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:20]1[NH2:21])(=[O:17])[CH3:16].Cl>C1C=CC=CC=1.N1C=CC=CC=1>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:21][C@@H:20]1[C@@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:27]([O:28][C:29](=[O:31])[CH3:30])[C@@H:32]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[O:33][CH:19]1[O:18][C:15](=[O:17])[CH3:16])=[O:7]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 120603-Iodobenzoic acidHCID 24386Thionyl ChlorideHCID 13059363glucosamine tetra-O-acetate

生成物 1

HCID 86744916N-(m-iodobenzoyl)-1,3,4,6-tetra-O-acetyl-D-glucosamine収率 45.1%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒2 回HCID 1049Pyridine溶媒

反応条件

温度
65 °C

実験手順

A mixture of m-iodobenzoic acid (1.6 g; 6.45×10-3 mol) and thionyl chloride (10 ml) was stirred at 65° C. for 24 hours, benzene was added thereto, and excessive thionyl chloride was removed by distillation under reduced pressure. The thus prepared m-iodobenzoyl chloride was dissolved in benzene (2 ml), and a solution of 1,3,4,6-tetra-O-acetyl-D-glucosamine (2 g; 5.76×10-3 mol) in benzene (10 ml) and pyridine (2 ml) was added thereto, followed by stirring for 48 hours. The resulting mixture was neutralized with 0.1N hydrochloric acid and extracted with chloroform, followed by crystallization from methanol to give N-(m-iodobenzoyl)-1,3,4,6-tetra-O-acetyl-D-glucosamine (ABGA) (1.50 g).

後処理

  1. customexcessive thionyl chloride was removed by distillation under reduced pressure
  2. dissolutionThe thus prepared m-iodobenzoyl chloride was dissolved in benzene (2 ml)
  3. stirringby stirring for 48 hours
  4. extractionextracted with chloroform
  5. customfollowed by crystallization from methanol

出典と根拠

ORDレコード
ord-e2a6f5ca54c547518b5178e2b31a1f0f
出典データセット
uspto-grants-1991_07
特許番号
US05034212

反応ノート

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