Dichloromethane → HCID 46870768, compound

HRID 1400221Notes

Reaction equation

HRID 1400221 reaction equation
[NH2:1][C:2](=[O:31])[CH:3]([OH:30])[CH:4]([NH:12][C:13]([C:15]1[C:16]([C:21]2[S:22][C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=3[N:25]=2)=[N:17][CH:18]=[CH:19][CH:20]=1)=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.ClCCl.ClC(Cl)C(O)=O>CS(C)=O>[NH2:1][C:2](=[O:31])[C:3](=[O:30])[CH:4]([NH:12][C:13]([C:15]1[C:16]([C:21]2[S:22][C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=3[N:25]=2)=[N:17][CH:18]=[CH:19][CH:20]=1)=[O:14])[CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6597Dichloroacetic AcidHCID 67541222HCID 67541222, compound

Product 1

HCID 46870768HCID 46870768, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of N-(4-Amino-3-hydroxy-4-oxo-1-phenylbutan-2-yl)-2-(1,3-benzothiazol-2-yl)pyridine-3-carboxamide (0.5 g, 1.16 mmol) in 1.5 ml of DMSO und 15 ml of dichloromethane 3.04 g N-cyclohexylcarbodiimid-N′-methylpolystyrole (1.9 mmol/g; 5.78 mmol) and 0.24 ml dichloroacetic acid (0.38 g, 2.89 mmol) were added, and the reaction mixture stirred over night at room temperature. For work up the polymer was filtered off, washed with dichloromethane, and the combined organic layers evaporated to dryness. Treatment with a mixture of n-hexane/ethylacetate, filtration and drying afforded 260 mg of the title compound, as white amorphous solid:

Workup

  1. filtrationFor work up the polymer was filtered off
  2. washwashed with dichloromethane
  3. customthe combined organic layers evaporated to dryness
  4. additionTreatment with a mixture of n-hexane/ethylacetate, filtration
  5. customdrying

Sources & evidence

ORD record
ord-703661a54e9f49eda6a95f16976dbc2c
Source dataset
uspto-grants-2014_12
Patent number
US08906941B2

Reaction notes

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