Benzyl isocyanate → HCID 60018596, compound

HRID 897077Notes

Reaction equation

HRID 897077 reaction equation
[CH2:1]([N:8]=[C:9]=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:11][CH2:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[C@@H:22]2[O:26][C@H:25]([C:27]([NH:29][CH2:30][CH3:31])=[O:28])[C@@H:24]([OH:32])[C@H:23]2[OH:33])=[C:15]([NH:34][CH2:35][CH:36]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[N:14]=1>ClCCl>[CH2:1]([NH:8][C:9]([NH:11][CH2:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[C@@H:22]2[O:26][C@H:25]([C:27]([NH:29][CH2:30][CH3:31])=[O:28])[C@@H:24]([OH:32])[C@H:23]2[OH:33])=[C:15]([NH:34][CH2:35][CH:36]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[N:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 59909598(2S,3S,4R,5R)-5-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide

Product 1

HCID 60018596HCID 60018596, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzylisocyanate (26 mg, 0.30 mmol) was added to a solution of (2S,3S,4R,5R)-5-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide (Preparation 11) in dichloromethane (2 ml). The reaction mixture was stirred for 16 hours at room temperature and allowed to evaporate. Ethanol (2 ml) was added and then aqueous hydrochloric acid (1 M, 1 ml) was added. The reaction mixture was stirred at 60° C. for 6 hours, then allowed to cool to room temperature and left for a further 16 h. More aqueous hydrochloric acid (1M, 0.5 ml) was added and the reaction mixture was stirred at room temperature for a further 4 h. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol (95:5 by volume) increasing in polarity to dichloromethane:methanol (90:10 by volume). The material obtained was impure and hence was repurified by column chromatography on silica gel eluting with dichloromethane:methanol (95:5 by volume) increasing in polarity to dichloromethane:methanol (90:10 by volume) to give the title compound as a solid (85 mg).

Workup

  1. customto evaporate
  2. additionEthanol (2 ml) was added
  3. additionaqueous hydrochloric acid (1 M, 1 ml) was added
  4. stirringThe reaction mixture was stirred at 60° C. for 6 hours
  5. temperatureto cool to room temperature
  6. waitleft for a further 16 h
  7. additionMore aqueous hydrochloric acid (1M, 0.5 ml) was added
  8. stirringthe reaction mixture was stirred at room temperature for a further 4 h
  9. customThe solvent was removed under reduced pressure
  10. customthe residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol (95:5 by volume)
  11. temperatureincreasing in polarity to dichloromethane:methanol (90:10 by volume)
  12. customThe material obtained
  13. customhence was repurified by column chromatography on silica gel eluting with dichloromethane:methanol (95:5 by volume)
  14. temperatureincreasing in polarity to dichloromethane:methanol (90:10 by volume)

Sources & evidence

ORD record
ord-e0ff6be8583f43e490b0b583d78b8f8f
Source dataset
uspto-grants-2005_07
Patent number
US06921753B2

Reaction notes

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