Cesium carbonate → HCID 59997292, compound

HRID 1815583Notes

Reaction equation

HRID 1815583 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([S:10]([N:13]([CH2:38][CH:39]([CH3:41])[CH3:40])[CH2:14][C@@H:15]([OH:37])[C@@H:16]([NH:25][C:26](=[O:36])[O:27][C@@H:28]3[C@H:35]4[C@H:31]([O:32][CH2:33][CH2:34]4)[O:30][CH2:29]3)[CH2:17][C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)(=[O:12])=[O:11])=[CH:9][C:4]=2[O:3][CH2:2]1.F[C:43]1[C:51]([N+:52]([O-:54])=[O:53])=[C:50]([N+]([O-])=O)[C:49]([N+:58]([O-:60])=[O:59])=[CH:48][C:44]=1[C:45]([OH:47])=[O:46].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[O:30]1[C@H:31]2[O:32][CH2:33][CH2:34][C@H:35]2[C@@H:28]([O:27][C:26]([NH:25][C@H:16]([C@H:15]([OH:37])[CH2:14][N:13]([S:10]([C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][O:3][C:4]=3[CH:9]=2)(=[O:12])=[O:11])[CH2:38][CH:39]([CH3:41])[CH3:40])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][C:48]3[C:49]([N+:58]([O-:60])=[O:59])=[CH:50][C:51]([N+:52]([O-:54])=[O:53])=[CH:43][C:44]=3[C:45]([OH:47])=[O:46])=[CH:20][CH:19]=2)=[O:36])[CH2:29]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 22500025HCID 22500025, compoundHCID 59997191(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl) (isobutyl)amino]-2-hydroxy-1-(4-hydroxybenzyl)propylcarbamate

Product 1

HCID 59997292HCID 59997292, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 59 mg (0.1 mMol) of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxy-1-(4-hydroxybenzyl)propylcarbamate, 50 of 2-fluoro-3,5-dinitronitrobenzoic acid and 65 mg (0.2 mMol) of cesium carbonate in 0.5 mL of dimethyl formamide was stirred at rt for 2 h. The mixture was diluted with ethyl acetate and extracted with 1N HCl. Evaporation of the solvent and chromatography on silica gel (5% methanolic ammonia in dichloromethane) gave the title compound (25 mg) as a yellow foam. H NMR: 0.82(6H,dd), 1.42(1H,m), 1.63(1H,m), 1.90(2H,m), 2.46(1H,dd), 2.8(1H,dd), 2.82-3.02(5H,m), 3.2(1H,m), 3.6-3.95(6H,m), 4.94(1H,q), 5.58(1H,d), 6.02(2H,s), 6.61(1H,d), 6.75(2H,d), 6.82(1H,d), 7.05(2H,d), 7.3(1H,d), 7.45(1H,s), 8.6(2H,ss).

Workup

  1. extractionextracted with 1N HCl
  2. customEvaporation of the solvent and chromatography on silica gel (5% methanolic ammonia in dichloromethane)

Sources & evidence

ORD record
ord-ad149c38ea844813a808dfc9d727b878
Source dataset
uspto-grants-2005_04
Patent number
US06878728B1

Reaction notes

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