Water → HCID 69312819, compound

HRID 1392403Notes

Reaction equation

HRID 1392403 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1([C:19]([NH:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH:34]=[O:35])[CH2:24][CH:23]2[OH:36])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11].C(=O)([O-])[O-].C1(C)C=CC(S([CH2:50][N:51]=[C:52]=O)(=O)=O)=CC=1.O>CO>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1([C:19]([NH:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]3[O:35][CH:52]=[N:51][CH:50]=3)[CH2:24][CH:23]2[OH:36])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 19660Carbonate IonHCID 117890781-Isocyanatomethanesulfonyl-4-methylbenzeneHCID 86601115HCID 86601115, compound

Product 1

HCID 69312819HCID 69312819, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-formylphenyl)piperidin-3-ol (3 g, 6 mmol) obtained in Step 1 of Example 61, photassium 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. 150 ml of water was added to the concentrated reaction mixture, which was then 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. extractionwas then extracted with dichloromethane
  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-e04f605b88174743883f39ebbceebac8
Source dataset
uspto-grants-2008_03
Patent number
US07342027B2

Reaction notes

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