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

HRID 1086976노트

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HRID 1086976 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 241Benzene용매2회HCID 1049Pyridine용매

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온도
65 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e2a6f5ca54c547518b5178e2b31a1f0f
출처 데이터셋
uspto-grants-1991_07
특허 번호
US05034212

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