p-Toluenesulfonic acid → HCID 59997257, compound

HRID 1815585Notes

Reaction equation

HRID 1815585 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([S:11]([N:14]([CH2:46][CH:47]([CH3:49])[CH3:48])[CH2:15][C@@H:16]([OH:45])[C@@H:17]([NH:33][C:34](=[O:44])[O:35][C@@H:36]3[C@H:43]4[C@H:39]([O:40][CH2:41][CH2:42]4)[O:38][CH2:37]3)[CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25]CC4C=CC=CC=4)=[CH:21][CH:20]=3)(=[O:13])=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.CO[C:52](OC)([CH3:54])[CH3:53].C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([S:11]([N:14]([CH2:15][C@H:16]3[O:45][C:52]([CH3:54])([CH3:53])[N:33]([C:34]([O:35][C@@H:36]4[C@H:43]5[C@H:39]([O:40][CH2:41][CH2:42]5)[O:38][CH2:37]4)=[O:44])[C@H:17]3[CH2:18][C:19]3[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=3)[CH2:46][CH:47]([CH3:48])[CH3:49])(=[O:12])=[O:13])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 59997272HCID 59997272, compound

Product 1

HCID 59997257HCID 59997257, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

250 mg of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(2,3-dihydro-1,4-benzodioxin-6-ylsulfonyl)(isobutyl)amino]-2-hydroxy-1-(4-benzyloxybenzyl)propylcarbamate, 2 mL of 2,2-dimethoxypropane, 0.5 g of p-toluenesulfonic acid in 50 mL of dichloromethane were refluxed for 3 h and then extracted with sodium bicarbonate solution. Chromatography on silica gel (1:1 ehtylacetate/hexanes) gave 220 mg of the desired compound as an oil which was dissolved in methanol and hydrogenated (at 50 psi) over 5% palladium on carbon. Filtration and evaporation of the volatiles gave the desired title compound as an oil

Workup

  1. extractionextracted with sodium bicarbonate solution

Sources & evidence

ORD record
ord-8749eb13120b4292a35a66e379efb96d
Source dataset
uspto-grants-2005_04
Patent number
US06878728B1

Reaction notes

Loading…