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

Reaction equation

HRID 5143 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-9334216d98874a0aa0f332578a5d0309
Source dataset
uspto-grants-1993_09
Patent number
US05243042

Linked notes

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