Potassium Hydroxide → HCID 86597505, compound

HRID 2354457Notes

Reaction equation

HRID 2354457 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([NH2:13])=[N:8][C:9]=2[O:11][CH3:12])[NH:4][N:3]=1.[OH-].[K+].Cl[CH:17]1[O:31][C@H:30]([CH2:32][O:33][C:34]([C:36]2[C:37]([CH3:42])=[CH:38][CH:39]=[CH:40][CH:41]=2)=[O:35])[C@@H:19]([O:20][C:21]([C:23]2[C:24]([CH3:29])=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:22])[CH2:18]1.C(OCC)(=O)C.CCCCCC>CO.C1(C)C=CC=CC=1>[CH3:38][C:39]1[CH:42]=[CH:37][C:36]([C:34]([O:33][CH2:32][C@@H:30]2[CH:19]([O:20][C:21]([C:23]3[CH:28]=[CH:27][C:26]([CH3:25])=[CH:29][CH:24]=3)=[O:22])[CH2:18][C@H:17]([N:4]3[C:5]4=[N:6][C:7]([NH2:13])=[N:8][C:9]([O:11][CH3:12])=[C:10]4[C:2]([I:1])=[N:3]3)[O:31]2)=[O:35])=[CH:41][CH:40]=1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 21226206Ethyl acetate hexaneHCID 68435941HCID 68435941, compoundHCID 178494242HCID 178494242, compound

Product 1

HCID 86597505HCID 86597505, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a suspension of (14) (6.68 g, 22.95 mmol) in 150 mL of methanol was added 8.05 mL of a 2.85 M methanolic potassium hydroxide. The mixture was stirred for one minute and then diluted with 100 mL of toluene and evaporated. The solid potassium salt of 1 was dried under vacuum. The potassium salt was suspended in 75 mL of anhydrous DMF and then diluted with 420 mL of anhydrous acetonitrile. 1-Chloro-1,2-dideoxy-3,5-di-O-toluoylribofuranose (8.95 g, 22.95 mmol) was immediately added and the reaction mixture was stirred at room temperature under argon for 1 h. and then filtered. The filtrate was evaporated and the residual foam was recrystallized twice from methanol: 6.59 g (45%) yield; TLC (1:1, ethyl acetate/hexane), Rf=0.52; 1H NMR (DMSO-d6) δ 7.93 and 7.37 (8H, m and d, J=7.9 Hz for the d, aromatic), 7.10 (2H, br s, 6-amino), 6.51 (1H, t, J=6.6 Hz, 1′-H), 5.69 (1H, m, 3′-H), 4.44 (3H, m, 4′- and 5′-Hs), 3.99 (3H, s, 4-methoxy), 3.19 and 2.63 (2H, 2×m, 2′-Hs), 2.40 and 2.38 (6H, 2×s, toluoyl methyl protons).

Workup

  1. customevaporated
  2. dry with materialThe solid potassium salt of 1 was dried under vacuum
  3. additiondiluted with 420 mL of anhydrous acetonitrile
  4. stirringthe reaction mixture was stirred at room temperature under argon for 1 h.
  5. filtrationfiltered
  6. customThe filtrate was evaporated
  7. customthe residual foam was recrystallized twice from methanol
  8. custom6.59 g (45%) yield

Sources & evidence

ORD record
ord-65b29e91f7d842818b9cff651d259eec
Source dataset
uspto-grants-2010_07
Patent number
US07751982B2

Reaction notes

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