p-Toluenesulfonic acid → HCID 86593025, compound

HRID 1815550Notes

Reaction equation

HRID 1815550 reaction equation
[CH2:1]([O:8][C:9]1[CH:48]=[CH:47][C:12]([CH2:13][C@H:14]([NH:35][C:36](=[O:46])[O:37][C@H:38]2[C@H:45]3[C@H:41]([O:42][CH2:43][CH2:44]3)[O:40][CH2:39]2)[C@H:15]([OH:34])[CH2:16][N:17]([CH2:30][CH:31]([CH3:33])[CH3:32])[S:18]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:51](OC)([CH3:53])[CH3:52].C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][C@H:14]2[C@@H:15]([CH2:16][N:17]([CH2:30][CH:31]([CH3:33])[CH3:32])[S:18]([C:21]3[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=3)(=[O:19])=[O:20])[O:34][C:51]([CH3:53])([CH3:52])[N:35]2[C:36]([O:37][C@H:38]2[C@H:45]3[C@H:41]([O:42][CH2:43][CH2:44]3)[O:40][CH2:39]2)=[O:46])=[CH:47][CH:48]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 86593024HCID 86593024, compound

Product 1

HCID 86593025HCID 86593025, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-[4-(benzyloxy)benzyl]-2-hydroxy-3-{isobutyl[(4-nitrophenyl)sulfonyl]amino}propylcarbamate (1.00 g, 1.5 mmol) in 20 mL of dichloromethane was added 2,2-dimethoxypropane (1.5 g, 14.6 mmol) and p-toluenesulfonic acid (0.09 g, 0.5 mmol). The solution was refluxed for 12 hours, and the solvent was removed under reduced pressure. The residue was purified on silica gel using ethyl acetate-hexanes (3.5:6.5) as eluent to provide 0.70 g (70%) of the title compound. 1H-NMR (CDCl3): δ 0.85 (3H,d), 0.90 (3H,d), 1.35,1.44 (3H,s)*,1.55,1.61 (3H,s)*, 1.84-2.00 (3H,m,b), 2.61-2.91 (4H,m), 2.91-3.08 (3H,m), 3.17,3.33 (1H,d)*, 3.56 (1H,t), 3.80-3.86 (2H,m), 3.91-3.98(1H,m), 4.23-4.27 (2H, m), 5.02-5.16 (2H,s), 5.67 (1H,d), 6.91 (2H,d), 7.03 (1H,d), 7.14 (1H,d), 7.31 (1H,d), 7.38 (2H,m), 7.45 (2H,d), 7.67 (2H,d), 8.25 (2H,d).

Workup

  1. temperatureThe solution was refluxed for 12 hours
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-a5f160fe48cd4652ba7983da8248d0e0
Source dataset
uspto-grants-2005_04
Patent number
US06878728B1

Reaction notes

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