Ethanol → HCID 16082777, compound

HRID 260158Notes

Reaction equation

HRID 260158 reaction equation
[CH2:1]([N:8]1[CH:25]=[N:24][C:23]2[N:13]([C@@H:14]3[O:22][C@H:19]([CH2:20][OH:21])[C@@H:17]([OH:18])[C@H:15]3[OH:16])[CH:12]=[N:11][C:10]=2[C:9]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27](Cl)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(Cl)(Cl)Cl.C(O)C>N1C=CC=CC=1>[C:27]([O:21][CH2:20][C@H:19]1[O:22][C@@H:14]([N:13]2[C:23]3[N:24]=[CH:25][N:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:9](=[O:26])[C:10]=3[N:11]=[CH:12]2)[C@H:15]([OH:16])[C@@H:17]1[OH:18])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6212ChloroformHCID 6456Trityl chloride2×HCID 14859922HCID 14859922, compound

Product 1

HCID 16082777HCID 16082777, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1-benzylinosine (3.58 g, 10 mmol) and trityl chloride (3.3 g, 12 mmol) in pyridine (50 mL is stirred overnight at room temperature. An additional amount of trityl chloride (3.3 g) is charged on the second and third days. The reaction is monitored by thin layer chromatography on silica gel plates using a mixture of chloroform and ethanol (10:1 v/v) as the developing solvent. After all the starting material is consumed, the mixture is concentrated in vacuo, and the residue coevaporated several times with toluene and ethanol, and then chromatographed on a silica column using chloroform-ethanol (19:1 v/v) as the eluent to give 5'-O-trityl-1-benzylinosine which is crystallized from ethanol: 5.40 g (90% yield), mp 208°-209° C. 1H NMR (Me2SO-d6) δ 3.20-3.24 (2H, m, H-5',5"), 4.10-4.29 (2H, m, H-3',4'), 4.61-4.67 (1H, m, H-2', collapsed to dd upon addition of D2O, J1',2' =5.6, J2',3' =5.0 Hz), 5.24 (2H, s, CH2Ph), 5.21-5.27 (1H, m, OH, exchangeable), 5.57 (1H, d, OH), 5.92 (1H, d, H-1'), 7.06-7.32 (2OH, m, Tr, CH2Ph), 8.23, 8.51 (1H each, H-2, H-8). Analyses: calculated for C26H32N4O5 : C, 71.98, H, 5.37, N, 9.33. Found: C, 71.86, H, 5.44, N, 9.18.

Workup

  1. customAfter all the starting material is consumed
  2. concentrationthe mixture is concentrated in vacuo
  3. customchromatographed on a silica column

Sources & evidence

ORD record
ord-92357d5077514e0595a2024ed6593f75
Source dataset
uspto-grants-1996_06
Patent number
US05525720

Reaction notes

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