Water → HCID 59009143, compound

HRID 545109Notes

Reaction equation

HRID 545109 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([S:13][CH2:14][C:15]([NH:17][CH2:18][C@@H:19]3[O:24][CH2:23][CH2:22][N:21]([CH2:25][C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=4)[CH2:20]3)=[O:16])[S:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[C:34](OC(=O)C)(=[O:36])[CH3:35].O>N1C=CC=CC=1>[NH:1]([C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([S:13][CH2:14][C:15]([NH:17][CH2:18][C@@H:19]3[O:24][CH2:23][CH2:22][N:21]([CH2:25][C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=4)[CH2:20]3)=[O:16])[S:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1)[C:34]([CH3:35])=[O:36]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 11591742HCID 11591742, compound

Product 1

HCID 59009143HCID 59009143, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of the resultant product (262 mg) of Example 9 in pyridine (2 mL) was added dropwise acetic anhydride (57 μL). The reaction mixture was stirred overnight at room temperature. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solvent of chloroform and methanol as an eluent. The solvent was evaporated from the eluent to give the title compound (279 mg) as a white amorphous solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography
  6. customThe solvent was evaporated from the eluent

Sources & evidence

ORD record
ord-7047098523864a4c9c3cd485a257e093
Source dataset
uspto-grants-2011_05
Patent number
US07935700B2

Reaction notes

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