Triethylamine → HCID 9831231, compound

HRID 1279205Notes

Reaction equation

HRID 1279205 reaction equation
[NH2:1][CH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[C@H:12]2[C@@H:16]3[O:17]C(C)(C)[O:19][C@@H:15]3[C@@H:14]([C:22]([NH:24][CH2:25][CH3:26])=[O:23])[O:13]2)=[C:5]([NH:27][CH2:28][CH:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:4]=1.C(N(CC)CC)C.[C:49]1([CH2:55][S:56](Cl)(=[O:58])=[O:57])[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>ClCCl>[CH2:55]([S:56]([NH:1][CH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[C@@H:12]2[O:13][C@H:14]([C:22]([NH:24][CH2:25][CH3:26])=[O:23])[C@@H:15]([OH:19])[C@H:16]2[OH:17])=[C:5]([NH:27][CH2:28][CH:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:4]=1)(=[O:58])=[O:57])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74740Phenylmethanesulfonyl chlorideHCID 69558158HCID 69558158, compound

Product 1

HCID 9831231HCID 9831231, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (3aS,4S,6R,6aR)-6-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide (Preparation 10) (120 mg, 0.21 mmol) and triethylamine (0.04 ml, 0.29 mmol) in anhydrous dichloromethane (2 ml) was treated with phenylmethylsulphonyl chloride (45 mg, 0.24 mmol). The mixture was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure and the residue dissolved in ethanol (1 ml). Hydrochloric acid (1M, 1 ml) was added to the solution and the mixture was heated at 60° C. for 8 hours. The solvent was removed under reduced pressure and the residue was azeotroped with ethanol (×2). The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane methanol (95:5 by volume) gradually changing to dichloromethane: methanol (90:10 by volume) to give a solid which was triturated with diethyl ether, diluted with pentane, filtered and dried to afford the title compound as a white solid (92 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in ethanol (1 ml)
  3. additionHydrochloric acid (1M, 1 ml) was added to the solution
  4. temperaturethe mixture was heated at 60° C. for 8 hours
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was azeotroped with ethanol (×2)
  7. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane methanol (95:5 by volume)
  8. customto give a solid which
  9. customwas triturated with diethyl ether
  10. additiondiluted with pentane
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-2fd55ec871e74e889e7772ca1bcc6c7f
Source dataset
uspto-grants-2002_09
Patent number
US06448236B1

Reaction notes

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