1,2-Dichloroethane → HCID 136005826, compound

HRID 915964Notes

Reaction equation

HRID 915964 reaction equation
ClCCCl.[CH:5]1([C:11]2[C:19]3[C:18](=[O:20])[NH:17][C:16]([C:21]4[CH:26]=[CH:25][C:24]([N:27]5[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]5)=[CH:23][C:22]=4[O:34][CH3:35])=[N:15][C:14]=3[N:13]([CH3:36])[N:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[CH3:37][NH2:38].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O.C(O)(=O)C>[CH:5]1([C:11]2[C:19]3[C:18](=[O:20])[NH:17][C:16]([C:21]4[CH:26]=[CH:25][C:24]([N:27]5[CH2:28][CH2:29][CH:30]([NH:38][CH3:37])[CH2:31][CH2:32]5)=[CH:23][C:22]=4[O:34][CH3:35])=[N:15][C:14]=3[N:13]([CH3:36])[N:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6329MethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 136005896HCID 136005896, compound

Product 1

HCID 136005826HCID 136005826, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a 4 ml 1,2-dichloroethane solution of 200 mg (0.46 mmol) of the compound obtained in Example 30, 100 μl (0.92 mmol) of methylamine (30% methanol solution), 146 mg (0.69 mmol) of sodium triacetoxyborohydride, and 26 μl of acetic acid were added, and the mixture was stirred at room temperature for 6 hours. Then, water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with water and a saturated aqueous solution of sodium chloride. After the washed layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/chloroform/methanol=10/10/1) to obtain 176 mg (85%) of the captioned compound.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with water
  3. dry with materialAfter the washed layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/chloroform/methanol=10/10/1)

Sources & evidence

ORD record
ord-705aeaa9036a4c4bab707342fb3e1f16
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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