Water → HCID 136005908, compound

HRID 915947Notes

Reaction equation

HRID 915947 reaction equation
C(Cl)Cl.[CH:4]1([N:10]2[C:18]3[C:17](=O)[NH:16][C:15]([C:20]4[CH:25]=[CH:24][C:23]([N:26]5[CH2:31][CH2:30][CH:29]([NH:32][CH3:33])[CH2:28][CH2:27]5)=[CH:22][C:21]=4[O:34][CH3:35])=[N:14][C:13]=3[C:12]([CH3:36])=[N:11]2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[C:37](OC(=O)C)(=[O:39])[CH3:38].N1C=CC=CC=1.[OH2:50]>>[CH:4]1([N:10]2[C:18]3[C:17](=[O:50])[NH:16][C:15]([C:20]4[CH:25]=[CH:24][C:23]([N:26]5[CH2:31][CH2:30][CH:29]([N:32]([CH3:33])[C:37](=[O:39])[CH3:38])[CH2:28][CH2:27]5)=[CH:22][C:21]=4[O:34][CH3:35])=[N:14][C:13]=3[C:12]([CH3:36])=[N:11]2)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

6

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 136080960HCID 136080960, compound

Product 1

HCID 136005908HCID 136005908, compoundYield 80%

Procedure

To a 4 ml methylene chloride solution of 105 mg (0.23 mmol) of the compound obtained in Example 92, 33 μl (0.35 mmoml) of acetic anhydride and 33.7 μl (0.47 mmoml) of pyridine were added, and the mixture was stirred at room temperature for 1 hour. Then, water was added to the reaction mixture, and the mixture was extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=60/1) to obtain 92 mg (80%) of the captioned compound.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform/methanol=60/1)

Sources & evidence

ORD record
ord-aff363b230d14c62828589c42ee6923d
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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