Triethylamine → HCID 66975627, compound

HRID 1022700Notes

Reaction equation

HRID 1022700 reaction equation
[NH2:1][CH2:2][C@H:3]1[C@H:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[O:8][CH2:7][CH2:6][N:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:4]1.C(N(CC)CC)C.Cl[CH2:33][CH2:34][S:35](Cl)(=[O:37])=[O:36]>C1COCC1.C(OCC)(=O)C>[Cl:17][C:12]1[CH:11]=[C:10]([C@@H:9]2[O:8][CH2:7][CH2:6][N:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:4][C@H:3]2[CH2:2][NH:1][S:35]([CH:34]=[CH2:33])(=[O:37])=[O:36])[CH:15]=[CH:14][C:13]=1[Cl:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 66975351HCID 66975351, compound

Product 1

HCID 66975627HCID 66975627, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (6R,7R)-6-(aminomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (633 mg) in THF (10 mL) were added triethylamine (0.705 mL) and 2-chloroethanesulfonyl chloride (0.213 mL) at 0° C., and the mixture was gradually warmed from 0° C. to room temperature, and stirred overnight. The reaction mixture was diluted with ethyl acetate. The diluted solution was washed with distilled water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (0.965 g).

Workup

  1. temperaturethe mixture was gradually warmed from 0° C. to room temperature
  2. washThe diluted solution was washed with distilled water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-913697a5c4a743269cac8938169ce4cf
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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