Dichloromethane → HCID 59035894, compound

HRID 1279212Notes

Reaction equation

HRID 1279212 reaction equation
C([O:9][C@@H:10]1[C@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@@H:13]([C:24]([NH:26][CH2:27][CH3:28])=[O:25])[O:12][C@H:11]1[N:29]1[CH:37]=[N:36][C:35]2[C:30]1=[N:31][C:32]([CH2:48][NH:49][S:50]([CH2:53][CH:54]([CH3:56])[CH3:55])(=[O:52])=[O:51])=[N:33][C:34]=2[NH:38][CH2:39][C:40]1[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=1)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].ClCCl>CO>[CH2:27]([NH:26][C:24]([C@@H:13]1[C@@H:14]([OH:15])[C@@H:10]([OH:9])[C@H:11]([N:29]2[CH:37]=[N:36][C:35]3[C:30]2=[N:31][C:32]([CH2:48][NH:49][S:50]([CH2:53][CH:54]([CH3:55])[CH3:56])(=[O:52])=[O:51])=[N:33][C:34]=3[NH:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=2)[O:12]1)=[O:25])[CH3:28]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 69558131HCID 69558131, compound

Product 1

HCID 59035894HCID 59035894, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (2R,3R,4S,5S)-4-(benzoyloxy)-5-[(ethylamino)carbonyl]-2-{2-{[(isobutylsulfonyl)amino]methyl}-6-[(4-methoxybenzyl)amino]-9H-purin-9-yl}tetrahydro-3-furanyl benzoate (Preparation 22) (40 mg, 0.05 mmol) in methanol (2 ml) was treated with potassium carbonate (28 mg, 0.20 mmol). The mixture was stirred at room temperature for 20 minutes after which time a precipitate had formed. Dichloromethane (10 ml) was added to the mixture to dissolve the precipitate. The mixture was then filtered and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol (95:5 by volume) to afford the title compound as a white solid (21 mg).

Workup

  1. customhad formed
  2. dissolutionto dissolve the precipitate
  3. filtrationThe mixture was then filtered
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol (95:5 by volume)

Sources & evidence

ORD record
ord-63ad4641e2ae42c0886bb5ee2645ae03
Source dataset
uspto-grants-2002_09
Patent number
US06448236B1

Reaction notes

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