Water → HCID 69331493, compound

HRID 2370927Notes

Reaction equation

HRID 2370927 reaction equation
[H-].[Na+].[C:3]([N:22]1[CH:26]=[C:25]([CH:27]([C:32]([O:34][CH3:35])=[O:33])[C:28]([O:30][CH3:31])=[O:29])[N:24]=[CH:23]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH2:36].C[N:38]([CH:40]=[O:41])[CH3:39]>>[C:27]([O:36][C:40]([NH:38][C:39]1[N:22]=[CH:3][C:4]([CH2:9][C:27]([C:25]2[N:24]=[CH:23][N:22]([C:3]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:26]=2)([C:32]([O:34][CH3:35])=[O:33])[C:28]([O:30][CH3:31])=[O:29])=[CH:5][CH:6]=1)=[O:41])([CH3:32])([CH3:28])[CH3:25]

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 69330958HCID 69330958, compound

Product 1

HCID 69331493HCID 69331493, compound

Conditions

Temperature
0 °C

Procedure

0.12 g (5.12 mmol, 50%) of sodium hydride was added to a solution of 2.25 g (5.11 mmol) of the compound from example 12b in 40 ml of dry DMF at 0° C. and stirred at this temperature for 5 min. The mixture was then allowed to reach RT, was stirred for 1 h, was again cooled to 0° C. and then 1.47 g (5.11 mmol) of the compound from example 1b were added in one portion. Stirring was continued at this temperature for 30 min, then 50 ml of water were added while cooling in ice, and the mixture was extracted three times with CH2Cl2. The combined organic phases were dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography on silica gel. 3.15 g of the title compound were obtained.

Workup

  1. customto reach RT
  2. stirringwas stirred for 1 h
  3. stirringStirring
  4. waitwas continued at this temperature for 30 min
  5. temperaturewhile cooling in ice
  6. extractionthe mixture was extracted three times with CH2Cl2
  7. dry with materialThe combined organic phases were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-b0d8c5f57ef64e1bace06367cd07094d
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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