Water → HCID 69203737, compound

HRID 2377267Notes

Reaction equation

HRID 2377267 reaction equation
[N:1]([CH2:4][C:5]1[S:9][C:8]([C:10]2[C:11]3[CH2:38][C:37]4[C:32](=[CH:33][CH:34]=[C:35]([CH2:39][N:40]5[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]5)[CH:36]=4)[C:12]=3[N:13]([CH:15]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[N:14]=2)=[CH:7][CH:6]=1)=[N+]=[N-].O>O1CCCC1>[CH3:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([CH:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[N:13]2[C:12]3[C:32]4[C:37]([CH2:38][C:11]=3[C:10]([C:8]3[S:9][C:5]([CH2:4][NH2:1])=[CH:6][CH:7]=3)=[N:14]2)=[CH:36][C:35]([CH2:39][N:40]2[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]2)=[CH:34][CH:33]=4)=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 962WaterHCID 91130494HCID 91130494, compound

Product 1

HCID 69203737HCID 69203737, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of Example 391 (7.1 g, 11.2 mmol) in tetrahydrofuran (150 mL) was added triphenylphosine (4.4 g, 16.9 mmol) and the mixture was heated to about 40° C. overnight. Water (15.2 mL) was added and heating to about 40° C. was continued for about 6 hours. The mixture was concentrated under vacuum, diluted with water, basified by addition of potassium carbonate and extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash chromatography on silica gel using dichloromethane/methanol (10:1)+1% ammonium hydroxide as eluent to provide the desired product. MS (ESI): m/z 606 (M+H)+.

Workup

  1. temperatureheating to about 40° C.
  2. concentrationThe mixture was concentrated under vacuum
  3. additiondiluted with water
  4. additionbasified by addition of potassium carbonate
  5. extractionextracted with ethyl acetate
  6. washThe combined organic extracts were washed with water and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-62fba2691b784682822808b4f95610c8
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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