Methanol → HCID 24893959, compound

HRID 473244Notes

Reaction equation

HRID 473244 reaction equation
[CH:1]1[C:18]2=[C:19]3[C:8]([C:9]4[C:20]5[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=5)[CH:12]=[CH:11][CH:10]=4)=[CH:7][CH:6]=[CH:5][C:4]3=[C:3]([C:21]#[C:22][C:23]2[C:24](=[O:43])[NH:25][C:26](=[O:42])[N:27]([CH:41]=2)[C@@H:28]2[O:40][C@H:31]([CH2:32][O:33]C(=O)C(C)(C)C)[CH2:30][CH2:29]2)[CH:2]=1.CO>C(O)(=O)C>[CH:1]1[C:18]2=[C:19]3[C:8]([C:9]4[C:20]5[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=5)[CH:12]=[CH:11][CH:10]=4)=[CH:7][CH:6]=[CH:5][C:4]3=[C:3]([C:21]#[C:22][C:23]2[C:24](=[O:43])[NH:25][C:26](=[O:42])[N:27]([CH:41]=2)[C@@H:28]2[O:40][C@H:31]([CH2:32][OH:33])[CH2:30][CH2:29]2)[CH:2]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 71589304HCID 71589304, compound

Product 1

HCID 24893959HCID 24893959, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of 5-(perylen-3-ylethynyl)-5′-O-pivaloyl-2′,3′-dideoxyuridine (350 mg, 0.613 mmol) in 80 mL of MeOH solid KOH (310 mg, 5.517 mmol) was added, and the mixture was stirred overnight. The mixture was then neutralized with acetic acid, evaporated under reduced pressure, co-evaporated with MeOH twice to give a crude product, which was chromatographically purified on a silica gel column using a 0 to 3% EtOH/CHCl3 gradient to give a chromatographically homogeneous (Rf 0.46, 37.5% acetone/CHCl3) product as orange solid (130 mg, 43%). 1H-NMR (DMSO-d6): 11.74 (s, 1H, NH), 8.76 (s, 1H, H-6), 8.45 (d, 1H, J 7.7), 8.41-8.38 (m, 2H), 8.36 (d, 1H, J 7.7), 8.30 (d, 1H, J 7.7), 7.71-7.54 (m, 6H) (perylenyl), 5.99-5.98 (m, 1H, H-1′), 5.35 (br. s, 1H, OH), 4.15-4.10 (m, 1H, H-4′), 3.70 (app. d, 1H, H-5′), 3.63 (app. d, 1H, H-5′), 2.38-2.31 (m, 1H, H-2′), 2.17-2.13 (m, 1H, H-2′), 2.01-1.94 (m, 1H, H-3′), 1.91-1.86 (m, 1H, H-3′).

Workup

  1. additionwas added
  2. customevaporated under reduced pressure, co-evaporated with MeOH twice
  3. customto give a crude product, which
  4. customwas chromatographically purified on a silica gel column

Sources & evidence

ORD record
ord-583168845cc34b78b87f2dc1ca7cd8ce
Source dataset
uspto-grants-2014_01
Patent number
US08633308B2

Reaction notes

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