Water → HCID 178418853, compound

HRID 10517

Reaction equation

HRID 10517 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12](OS(C)(=O)=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si]([N:24]=[N+:25]=[N-:26])(C)C.[F-].[Cs+].O>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([N:24]=[N+:25]=[N-:26])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 25953Cesium fluorideHCID 78378AzidotrimethylsilaneHCID 178418975HCID 178418975, compound

Product 1

HCID 178418853HCID 178418853, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Intermediate 36 (196 g) and trimethylsilyl azide (283 ml, Tokyo Kasei Kogyo) in dimethylformamide (667 ml) was added with cesium fluoride (305 g, Wako Pure Chemical Industries) with stirring and stirred at 70° C. for 4 days. The reaction mixture was cooled to room temperature and then added twice with water in a volume of 2.75 l in total. This reaction mixture was stirred with ice cooling for 2 hours, and the deposited precipitates were collected by filtration. Then, the precipitates were washed with water to obtain a roughly purified product of the title compound (142 g).

Workup

  1. stirringstirred at 70° C. for 4 days
  2. stirringThis reaction mixture was stirred with ice cooling for 2 hours
  3. customthe deposited precipitates
  4. filtrationwere collected by filtration
  5. washThen, the precipitates were washed with water

Sources & evidence

ORD record
ord-b811f8e37f91454ca9c82dfe2654d854
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Linked notes

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