Triethylamine → HCID 33037887, compound

HRID 1505622Notes

Reaction equation

HRID 1505622 reaction equation
[C:1]1([CH2:7][S:8](Cl)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C@@H:19]([NH2:21])[CH3:20])=[CH:15][CH:14]=1.C(N(CC)CC)C>ClCCl>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C@@H:19]([NH:21][S:8]([CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:10])=[O:9])[CH3:20])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74740Phenylmethanesulfonyl chlorideHCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamine

Product 1

HCID 33037887HCID 33037887, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenylmethanesulfonyl chloride (28.1 g, 147.7 mmol) was added into a solution of (S)-1-(4-bromophenyl)ethanamine (28.0 g, 140.7 mmol) and triethylamine (21.3 g, 211.1 mmol) in dichloromethane (400 mL) drop wise at 0° C. The reaction mixture was stirred at ambient temperature for 12 hours. The reaction solution was then washed with dilute aqueous HCl, saturated aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered, and concentrated to provide the title compound (35.3 g, 71% yield) as pale yellow solid which was used in the next step without further purification.

Workup

  1. washThe reaction solution was then washed with dilute aqueous HCl, saturated aqueous NaHCO3 and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0d7418ab281e4c31bd501a146161c214
Source dataset
uspto-grants-2015_12
Patent number
US09216988B2

Reaction notes

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