Potassium Carbonate → HCID 69315069, compound

HRID 1392422Notes

Reaction equation

HRID 1392422 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]=3C=O)[CH2:20][C:19]2=[O:33])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7].[C:34](=[O:37])([O-])[O-].[K+].[K+].C1(C)C=CC(S([CH2:49][N:50]=[C:51]=O)(=O)=O)=CC=1>CO>[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[C:49]3[N:50]=[CH:51][O:37][CH:34]=3)[CH2:20][CH:19]2[OH:33])=[O:16])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1)=[O:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10253489HCID 10253489, compoundHCID 117890781-Isocyanatomethanesulfonyl-4-methylbenzene

Product 1

HCID 69315069HCID 69315069, compoundYield 107.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of 4-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(4-fluoro-2-formylhenyl)piperidin-3-ol (3.0 g, 6 mmol) obtained in Example 79, potassium carbonate (2 g, 20 mmol) and p-toluenesulfonylmethyl isocyanate (TosMIC; 1.8 g, 9 mmol) was refluxed in 500 ml of methanol for about 2 hours. The reaction mixture was concentrated, added water thereto, and extracted with dichloromethane. The resulting organic layer was dried and concentrated on sodium sulfate. The resulting residue was purified with column chromatography to give 3.2 g of the titled compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionadded water
  3. extractionextracted with dichloromethane
  4. customThe resulting organic layer was dried
  5. concentrationconcentrated on sodium sulfate
  6. customThe resulting residue was purified with column chromatography

Sources & evidence

ORD record
ord-9e2514a48a2844c7bb07516053bcf7f2
Source dataset
uspto-grants-2008_03
Patent number
US07342027B2

Reaction notes

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