HCID 21998635, 화합물 → HCID 21998625, 화합물

HRID 1976559노트

반응식

HRID 1976559 반응식
[NH2:1][C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:10]=2)[C:6](=[S:25])[NH:5][C:4](=[O:26])[C:3]=1[NH:27][C:28](=O)[C:29]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([CH3:31])[CH3:30].CC([O-])(C)C.[K+]>C(O)(C)C.ClCCl>[CH2:18]([O:17][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=1[O:15][CH3:16])[CH2:8][N:7]1[C:2]2[N:1]=[C:28]([C:29]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([CH3:30])[CH3:31])[NH:27][C:3]=2[C:4](=[O:26])[NH:5][C:6]1=[S:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

참가 물질

5

반응물 2

HCID 21998635HCID 21998635, 화합물HCID 23665647Potassium tert-butoxide

생성물 1

HCID 21998625HCID 21998625, 화합물수율 69.9%

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 6344Dichloromethane용매

실험 절차

6-Amino-1-(3 -benzyloxy-4-methoxy-benzyl)-5-(2-benzyloxy-2-methyl-propionylamino)-2-thiouracil (46.54 g, 83 mmole) and 97% t-BuOK (38.41 g, 332 mmole) were heated under reflux in isopropanol (460 ml) for 50 minutes. The solvent was removed in vacuo, the residue dissolved in water (300 ml), treated twice with 5 g of charcoal, filtered, water added to a total volume of 500 ml and pH adjusted to neutral with a mixture of 5M HCl (60 ml) and sodium bicarbonate solution. The solid was collected at 10° C. to give 41.62 g of crude product, which was dissolved in dichloromethane (60 ml) and chromatographed over silicagel (126 g) using dichloromethane as eluant. Crystallization from methanol gave 3-(3-benzyloxy-4-methoxy-benzyl)-8-(1-benzyloxy-1-methyl-ethyl)-2-thioxanthine, (31.5 g, 69.9%) mp 290-302° C. (dec).

후처리

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in water (300 ml)
  3. additiontreated twice with 5 g of charcoal
  4. filtrationfiltered
  5. additionwater added to a total volume of 500 ml
  6. additionneutral with a mixture of 5M HCl (60 ml) and sodium bicarbonate solution
  7. customThe solid was collected at 10° C.
  8. customto give 41.62 g of crude product, which
  9. customchromatographed over silicagel (126 g)
  10. customCrystallization from methanol

출처 및 근거

ORD 기록
ord-7e555f6182354e258ca654dc15cd4025
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06228859B1

반응 노트

불러오는 중…