Sodium t-butoxide → HCID 69315548, compound

HRID 1392418Notes

Reaction equation

HRID 1392418 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][C:9]1([C:15]([NH:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=3[NH:31][C:32](=[O:38])[C:33]([CH3:37])([CH3:36])[CH2:34]Cl)[CH2:20][CH:19]2[OH:39])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7].CC(C)([O-])C.[Na+]>ClCCl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][C:9]1([C:15]([NH:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=3[N:31]3[CH2:34][C:33]([CH3:37])([CH3:36])[C:32]3=[O:38])[CH2:20][CH:19]2[OH:39])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7]

Participants

4

Reactant 2

HCID 23676156Sodium t-butoxideHCID 69315543HCID 69315543, compound

Product 1

HCID 69315548HCID 69315548, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The solution of 4-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-[4-fluoro-2-(3-chloro-2,2-dimethylpropionyl)aminophenyl]piperidin-3-ol (1.1 g) obtained in Step 1 in 40 ml of dichloromethane was cooled to 0° C. and was added sodium tert-butoxide (NaOtBu, 600 mg) thereto. The reaction mixture was stirred overnight at room temperature, diluted with dichloromethane, and washed with brine. The resulting organic layer was dried and concentrated on sodium sulfate. The resulting residue was purified with column chromatography to give 762 mg of the titled compound.

Workup

  1. washwashed with brine
  2. customThe resulting organic layer was dried
  3. concentrationconcentrated on sodium sulfate
  4. customThe resulting residue was purified with column chromatography

Sources & evidence

ORD record
ord-60e03ed85c724396a695b90690f854c4
Source dataset
uspto-grants-2008_03
Patent number
US07342027B2

Reaction notes

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