2-Propanesulfonyl chloride → HCID 9894877, compound

HRID 2268361Notes

Reaction equation

HRID 2268361 reaction equation
[CH:1]([S:4](Cl)(=[O:6])=[O:5])([CH3:3])[CH3:2].[NH2:8][CH2:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[CH:15][N:16]2[C@H:19]2[C@H:23]([OH:24])[C@H:22]([OH:25])[C@@H:21]([CH2:26][O:27][CH3:28])[O:20]2)=[C:12]([NH:29][CH2:30][CH:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:11]=1>N1C(C)=CC=CC=1C>[OH:24][C@@H:23]1[C@H:22]([OH:25])[C@@H:21]([CH2:26][O:27][CH3:28])[O:20][C@H:19]1[N:16]1[CH:15]=[N:14][C:13]2[C:17]1=[N:18][C:10]([CH2:9][NH:8][S:4]([CH:1]([CH3:3])[CH3:2])(=[O:6])=[O:5])=[N:11][C:12]=2[NH:29][CH2:30][CH:31]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 824082-Propanesulfonyl chloride3×HCID 9897827(2R,3R,4S,5R)-2-{2-(Aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

Product 1

HCID 9894877HCID 9894877, compoundYield 24.7%

Reagents, catalysts & solvents 1

HCID 79372,6-LutidineSolvent2×

Procedure

Isopropylsulphonyl chloride (120 mg, 0.84 mmol) was added to a stirred solution of (2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino}-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (408 mg, 0.8 mmol) (example 1) in 2,6-lutidine (10 ml). The mixture was stirred at room temperature for 24 hr followed by stirring at 50° C. for a further 5 days. A second portion of isopropylsulphonyl chloride (120 mg, 0.84 mmol) and lutidine (4 ml) were added and the reaction stirred at 50° C. for 24 hr. A third portion of isopropylsulphonyl chloride (120 mg, 0.84 mmol) was added and heating at 50° C. continued for a further 24 hr. At the end of this period the solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and aqueous ammonia. The organic phase was separated and the solvent removed under reduced pressure to give a residue which was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (98:2:0.1) increasing to dichloromethane:methanol:ammonia (96:4:0.2). This gave the title compound (118 mg) as an oil. MS: 597 (MH+).

Workup

  1. stirringby stirring at 50° C. for a further 5 days
  2. stirringthe reaction stirred at 50° C. for 24 hr
  3. temperatureheating at 50° C.
  4. waitcontinued for a further 24 hr
  5. customAt the end of this period the solvent was removed under reduced pressure
  6. customthe residue partitioned between ethyl acetate and aqueous ammonia
  7. customThe organic phase was separated
  8. customthe solvent removed under reduced pressure
  9. customto give a residue which
  10. customwas purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (98:2:0.1)
  11. temperatureincreasing to dichloromethane:methanol:ammonia (96:4:0.2)

Sources & evidence

ORD record
ord-6820248640234a7ea192d6f99cad9289
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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