Cesium carbonate → HCID 59997206, compound

HRID 1815586Notes

Reaction equation

HRID 1815586 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([S:11]([N:14]([CH2:19][C@H:20]3[O:24][C:23]([CH3:26])([CH3:25])[N:22]([C:27]([O:29][C@@H:30]4[C@H:37]5[C@H:33]([O:34][CH2:35][CH2:36]5)[O:32][CH2:31]4)=[O:28])[C@H:21]3[CH2:38][C:39]3[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=3)[CH2:15][CH:16]([CH3:18])[CH3:17])(=[O:13])=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.Cl.[N:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1[CH2:53]Cl.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([S:11]([N:14]([CH2:19][C@H:20]3[O:24][C:23]([CH3:26])([CH3:25])[N:22]([C:27]([O:29][C@@H:30]4[C@H:37]5[C@H:33]([O:34][CH2:35][CH2:36]5)[O:32][CH2:31]4)=[O:28])[C@H:21]3[CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH2:53][C:48]4[CH:49]=[CH:50][CH:51]=[CH:52][N:47]=4)=[CH:41][CH:40]=3)[CH2:15][CH:16]([CH3:17])[CH3:18])(=[O:12])=[O:13])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 23392Picolyl chloride hydrochlorideHCID 59997257HCID 59997257, compound

Product 1

HCID 59997206HCID 59997206, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.1 g of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (4S,5R)-5-{[(2,3-dihydro-1,4-benzodioxin-6-ylsulfonyl)(isobutyl)amino]methyl}-4-(4-hydroxybenzyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate, 0.03 g of o-picolylchloride-hydrochloride and 0.15 g of cesium carbonate were suspended in 0.5 mL of dimethyl formamide and heated to 60 degrees for 3 h. The mixture was diluted with ethyl acetate and washed with water. Chromatography on silica gel (9:1 ethyl acetate/hexanes) gave 72 mg of the desired material

Workup

  1. temperatureheated to 60 degrees for 3 h
  2. washwashed with water

Sources & evidence

ORD record
ord-bb58a22453614c1d9488153bf843ed5c
Source dataset
uspto-grants-2005_04
Patent number
US06878728B1

Reaction notes

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