Cesium carbonate → HCID 23500250, compound

HRID 1835873Notes

Reaction equation

HRID 1835873 reaction equation
[CH2:1]([O:5][C:6]([N:8]([S:35]([C:38]1[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=1)(=[O:37])=[O:36])[CH2:9][CH2:10][N:11]([S:25]([C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1)(=[O:27])=[O:26])[CH2:12][CH2:13][NH:14][S:15]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)(=[O:17])=[O:16])=[O:7])[CH2:2][CH2:3][CH3:4].Br[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][OH:55].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([O:5][C:6]([N:8]([S:35]([C:38]1[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=1)(=[O:37])=[O:36])[CH2:9][CH2:10][N:11]([S:25]([C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1)(=[O:26])=[O:27])[CH2:12][CH2:13][N:14]([S:15]([C:18]1[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=1)(=[O:16])=[O:17])[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][OH:55])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1087001-Nonanol, 9-bromo-HCID 23500252HCID 23500252, compound

Product 1

HCID 23500250HCID 23500250, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 14 g of 1-butoxycarbonyl-1,4,7-tri-(p-toluenesulfonyl)-1,4,7-triazaheptane, 7.04 g of 9-bromo-1-nonanol, and 34.25 g of Cs2CO3 in 700 ml of DMF was stirred at 65° C. for 24 hours. The mixture was cooled and concentrated under reduced pressure. CH2Cl2 was added and the remaining solid was filtered and discarded. The solvent was evaporated to give 22.17 g of crude product which was purified on silica gel and eluted with CH2Cl2/ethyl acetate (50/1-20/1 v/v). 7.95 g of pure product was obtained. The preparation scheme is shown below:

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. additionCH2Cl2 was added
  4. filtrationthe remaining solid was filtered
  5. customThe solvent was evaporated
  6. customto give 22.17 g of crude product which
  7. customwas purified on silica gel
  8. washeluted with CH2Cl2/ethyl acetate (50/1-20/1 v/v)

Sources & evidence

ORD record
ord-ecc5527651c34068b3176f4d1553902f
Source dataset
uspto-grants-2004_08
Patent number
US06774082B2

Reaction notes

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