1,1'-(Diazomethylene)bis(benzene) → 5-amino-1-(2,3,5-tris-O-acetyl-beta-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid diphenylmethyl ester

HRID 5143

반응식

HRID 5143 반응식
[C:1]1([C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N+]=[N-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:16][C:17]1[N:21]([C@@H:22]2[O:34][C@H:33]([CH2:35][O:36][C:37](=[O:39])[CH3:38])[C@@H:28]([O:29][C:30](=[O:32])[CH3:31])[C@H:23]2[O:24][C:25](=[O:27])[CH3:26])[CH:20]=[N:19][C:18]=1[C:40]([OH:42])=[O:41]>C(Cl)Cl>[C:1]1([CH:7]([O:42][C:40]([C:18]2[N:19]=[CH:20][N:21]([C@@H:22]3[O:34][C@H:33]([CH2:35][O:36][C:37](=[O:39])[CH3:38])[C@@H:28]([O:29][C:30](=[O:32])[CH3:31])[C@H:23]3[O:24][C:25](=[O:27])[CH3:26])[C:17]=2[NH2:16])=[O:41])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

4

반응물 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 118111085-amino-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)imidazole-4-carboxylic acid

생성물 1

HCID 544043805-amino-1-(2,3,5-tris-O-acetyl-beta-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid diphenylmethyl ester수율 88%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Diphenyldiazomethane (2.0 g, 10.3 mmol) was added to the suspension of 5-amino-1-(2,3,5-tris-O-acetyl-β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid (3.86 g, 10 mmol) in CH2Cl2 (50 mL). The mixture was stirred at room temperature for 16 h, by which time all the reactants had dissolved. The reaction mixture was poured onto the top of a column of silica gel (100 g, packed in CH2Cl2, collected 100-mL fractions), and the column was washed with 5% EtOAc in CH2Cl2 (300 mL), then the product was eluted with 40% EtOAc in CH2Cl2. Fractions 5 to 10 were combined and concentrated, then pumped under high vacuum overnight to give 5-amino-1-(2,3,5-tris-O-acetyl-β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid diphenylmethyl ester as a pale yellow foam: 4.86 g (88% yield); IR (CHCl3) 3445, 3345, 1752, and 1678 cm-1 ; HRMS (EI) m/z found 551.1870 [calcd for C28H29N3O9, 551.1904 (M+)]; NMR (CDCl3) δ2.13 (s, 9), 4.32 (d of d, 1,J=12 and 3 Hz), 4.40 (m, 1), 4.47 (d of d, 1,J=12 and 3 Hz), 5.30 (m, 1), 5.45 (t, 1, J=5 Hz), 5.48 (s, 2), 5.67 (d, 1, J=5 Hz), 7.08 (s, 1), 7.25 (m, 3), 7.32 (t, 4,J=7 Hz), UV max (CH3OH) 267 nm (ε12510).

후처리

  1. dissolutionhad dissolved
  2. additionThe reaction mixture was poured onto the top of a column of silica gel (100 g, packed in CH2Cl2, collected 100-mL fractions)
  3. washthe column was washed with 5% EtOAc in CH2Cl2 (300 mL)
  4. washthe product was eluted with 40% EtOAc in CH2Cl2
  5. concentrationconcentrated
  6. custompumped under high vacuum overnight

출처 및 근거

ORD 기록
ord-9334216d98874a0aa0f332578a5d0309
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05243042

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