Triethylamine → HCID 86663847, compound

HRID 1022547Notes

Reaction equation

HRID 1022547 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH:10]2[CH2:23][OH:24])[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:11][CH:10]2[CH2:23][O:24][S:33]([CH3:32])(=[O:35])=[O:34])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 66975761HCID 66975761, compound

Product 1

HCID 86663847HCID 86663847, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (6RS,7SR)-7-(3,4-dichlorophenyl)-6-(hydroxymethyl)-1,4-oxazepane-4-carboxylate (735 mg) in THF (10 ml) were added triethylamine (0.41 mL) and methanesulfonyl chloride (0.21 mL) under ice-cooling, and the mixture was stirred for 1 hr. Triethylamine (0.14 ml) and methanesulfonyl chloride (0.076 ml) were added, and the mixture was stirred for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate. The diluted solution was washed with 1 N hydrochloric acid, distilled water and brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (863 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with ethyl acetate
  5. washThe diluted solution was washed with 1 N hydrochloric acid
  6. distillationdistilled water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-649858fc3c68404c9f7bbee826efe8cf
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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