Hydrochloric Acid → HCID 33037884, compound

HRID 1505624Notes

Reaction equation

HRID 1505624 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.O.Cl>N1C=CC=CC=1>[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 74740Phenylmethanesulfonyl chlorideHCID 853000(R)-4-bromo-alpha-methylbenzylamine

Product 1

HCID 33037884HCID 33037884, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
10 °C

Procedure

Phenylmethanesulfonyl chloride (10.5 g, 55 mmol) was added into a solution of (R)-1-(4-bromophenyl)ethanamine (10 g, 50 mmol) in pyridine (100 mL) drop wise at 0° C. The reaction mixture was stirred at 10° C. for 1 hour. The reaction was poured into water (500 mL), the pH value adjusted to 5 with 6 N aqueous HCl, extracted with EtOAc (100 mL×4). The organic layer was dried over Na2SO4, filtered, and concentrated to provide the title compound (13 g, 73% yield) as pale yellow solid which was used in the next step without further purification.

Workup

  1. extractionextracted with EtOAc (100 mL×4)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-88c5195c314c4f3fbb4b489f3ffb942a
Source dataset
uspto-grants-2015_12
Patent number
US09216988B2

Reaction notes

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