Methanol → HCID 178474860, compound

HRID 1602155Notes

Reaction equation

HRID 1602155 reaction equation
[N:1]([Si](C)(C)C)=[N+:2]=[N-:3].C([Sn](=O)CCCC)CCC.[F:18][C:19]1[CH:20]=[C:21]([N:33]2[CH2:37][C@H:36]([CH2:38][NH:39][C:40](=[O:42])[CH3:41])[O:35][C:34]2=[O:43])[CH:22]=[CH:23][C:24]=1[C:25]1[CH2:30][CH2:29][N:28]([C:31]#[N:32])[CH2:27][CH:26]=1.CO>C1(C)C=CC=CC=1>[F:18][C:19]1[CH:20]=[C:21]([N:33]2[CH2:37][C@H:36]([CH2:38][NH:39][C:40](=[O:42])[CH3:41])[O:35][C:34]2=[O:43])[CH:22]=[CH:23][C:24]=1[C:25]1[CH2:30][CH2:29][N:28]([C:31]2[NH:32][N:3]=[N:2][N:1]=2)[CH2:27][CH:26]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 57025622HCID 57025622, compound

Product 1

HCID 178474860HCID 178474860, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Azidotrimethylsilane (154 mg) and dibutyltin oxide (97 mg) were added to a stirred suspension of Example 24 (240 mg) in dry toluene (10 ml), and the mixture stirred at 70° C. for 18 hours. On cooling, methanol (5 ml) was added and after stirring for 10 minutes the solvent was evaporated. The title compound was isolated by MPLC (20% MeOH/CH2Cl2, Merck 9385 silica) and crystallised on evaporating the fractions to a small volume. The title product was filtered off washed with a little cold methanol (150 mg, 56%).

Workup

  1. temperatureOn cooling
  2. stirringafter stirring for 10 minutes the solvent
  3. customwas evaporated

Sources & evidence

ORD record
ord-70ffde6cee31457e9194c75d6e0fe9a4
Source dataset
uspto-grants-1999_11
Patent number
US05981528

Reaction notes

Loading…