HCID 178489550, compound → HCID 178489549, compound

HRID 440613Notes

Reaction equation

HRID 440613 reaction equation
[CH3:1][O:2][C:3]1[CH:65]=[CH:64][CH:63]=[CH:62][C:4]=1[C:5]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[CH:33]=[C:31]([CH3:32])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[CH2:22][C@@H:21]1[O:34][PH:35]([O:37][CH2:38][C@H:39]1[O:43][C@@H:42]([N:44]2[CH:52]=[C:50]([CH3:51])[C:48](=[O:49])[NH:47][C:45]2=[O:46])[CH2:41][C@@H:40]1[O:53]C(=O)C1C=CC=CC=1)=[O:36])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CO.C(N)(C)(C)C>[CH3:1][O:2][C:3]1[CH:65]=[CH:64][CH:63]=[CH:62][C:4]=1[C:5]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[CH:33]=[C:31]([CH3:32])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[CH2:22][C@@H:21]1[O:34][PH:35]([O:37][CH2:38][C@H:39]1[O:43][C@@H:42]([N:44]2[CH:52]=[C:50]([CH3:51])[C:48](=[O:49])[NH:47][C:45]2=[O:46])[CH2:41][C@@H:40]1[OH:53])=[O:36])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

3

Reactant 1

HCID 178489550HCID 178489550, compound

Product 1

HCID 178489549HCID 178489549, compound

Reagents, catalysts & solvents 1

HCID 22156075HCID 22156075, compoundSolvent

Procedure

Dinucleoside monophosphate 3 (20 mg; 20 μmol) was dissolved in 2 mL of 1:1 CH3OH-t-butylamine. The reaction mixture was maintained at 40°-45° C. for 2 days, then concentrated under diminished pressure. The residue was purified by preparative silica gel TLC; development was with 9:1 CH2Cl2 -CH3OH. Dinucleoside monophosphate 4 was isolated as an off-white gummy solid following lyophilization, yield 15 mg (84%); silica gel TLC Rf 0.50 (10:1 CH2Cl2 -CH3OH); 1H-NMR (CDCl3, (CH3)4Si) & 0.8-0.9 (m), 1.2-1.35 (m), 1.32 (s), 1.81 (s), 2.1-2.9 (m), 3.00 (m), 3.4-4.3 (m), 3.71 (s), 4.4 (m), 4.6 (m), 5.04 (m), 6.07 (t), 6.35 (m), 6.78 (d), 7.2-7.4 (m), 7.50 (s) and 8.46 (br s).

Workup

  1. temperatureThe reaction mixture was maintained at 40°-45° C. for 2 days
  2. concentrationconcentrated under diminished pressure
  3. customThe residue was purified by preparative silica gel TLC

Sources & evidence

ORD record
ord-d41e4215b9974ad6ba2683fe7b66c200
Source dataset
uspto-grants-1996_05
Patent number
US05519126

Reaction notes

Loading…