Cesium carbonate → HCID 88006679, compound

HRID 1582526Notes

Reaction equation

HRID 1582526 reaction equation
[CH3:1][Si:2]([CH3:42])([CH2:21][CH2:22][C:23]([F:41])([F:40])[C:24]([F:39])([F:38])[C:25]([F:37])([F:36])[C:26]([F:35])([F:34])[C:27]([F:33])([F:32])[C:28]([F:31])([F:30])[F:29])[CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:19]=[CH:18][C:17]([OH:20])=[CH:16][N:15]=2)=[CH:10][CH:9]=1.[CH2:43]([CH:47]1[CH2:51][C:50](=[O:52])[O:49][CH:48]1[CH2:53]OS(C1C=CC(C)=CC=1)(=O)=O)[CH:44]([CH3:46])[CH3:45].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:42][Si:2]([CH3:1])([CH2:21][CH2:22][C:23]([F:41])([F:40])[C:24]([F:38])([F:39])[C:25]([F:36])([F:37])[C:26]([F:34])([F:35])[C:27]([F:32])([F:33])[C:28]([F:29])([F:30])[F:31])[CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[CH:16][C:17]([O:20][CH2:53][CH:48]3[O:49][C:50](=[O:52])[CH2:51][CH:47]3[CH2:43][CH:44]([CH3:46])[CH3:45])=[CH:18][N:19]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 20726309HCID 20726309, compoundHCID 22717501HCID 22717501, compound

Product 1

HCID 88006679HCID 88006679, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of compound 47 (0.162 g, 0.250 mmol), toluene-4-sulfonic acid 3-isobutyl-5-oxo-tetrahydro-furan-2-ylmethyl ester (0.0815 g, 0.250 mmol) and cesium carbonate (0.098 g, 0.300 mmol) in DMF 5.0 ml) was stirred at room temperature for 24 h. The reaction mixture was washed with water and the organic layer extracted into ethyl acetate/hexane (3×20 ml, 1:1). The combine extracts were washed with brine, dried (MgSO4) and the solvent removed in vacuo. The residues were purified by column chromatography [silica gel, hexane/ethyl acetate (9:1)] to yield a colorless solid, which was recrystallized from acetonitrile.

Workup

  1. washThe reaction mixture was washed with water
  2. extractionthe organic layer extracted into ethyl acetate/hexane (3×20 ml, 1:1)
  3. washThe combine extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customThe residues were purified by column chromatography [silica gel, hexane/ethyl acetate (9:1)]
  7. customto yield a colorless solid, which
  8. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-393d64d909a646e7abe7e95f775ad203
Source dataset
uspto-grants-2004_05
Patent number
US06737124B2

Reaction notes

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