Water → HCID 86760998, compound

HRID 1437645Notes

Reaction equation

HRID 1437645 reaction equation
Cl.[CH:2]([C@H:15]1[C@@H:20]([O:21][CH2:22][C:23]2[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:24]=2)[CH2:19][CH2:18][NH:17][CH2:16]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CCN(CC)CC.[CH3:44][N:45]=[C:46]=[O:47].O>C1COCC1>[CH:2]([C@H:15]1[C@@H:20]([O:21][CH2:22][C:23]2[CH:28]=[C:27]([C:29]([F:30])([F:31])[F:32])[CH:26]=[C:25]([C:33]([F:36])([F:34])[F:35])[CH:24]=2)[CH2:19][CH2:18][N:17]([C:46]([NH:45][CH3:44])=[O:47])[CH2:16]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 86760996HCID 86760996, compound

Product 1

HCID 86760998HCID 86760998, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound (31.8 mg) obtained in Example 25 and Et3N (8.4 μl) in THF (3 ml), methyl isocyanate (6.8 mg) was added, and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into water, and then the product was extracted with ethyl acetate. The organic layer was washed with an aqueous 10% citric acid solution and saturated brine, and dried, and the solvent was evaporated under reduced pressure, and then the residue was purified by preparative HPLC to obtain the title compound.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous 10% citric acid solution and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-2ef36cf767dd458b8c5710803012080d
Source dataset
uspto-grants-2009_11
Patent number
US07622487B2

Reaction notes

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