Hydrochloric Acid → (S)-tert-butyl (2-amino-2-(3-bromo-5-fluorophenyl)ethyl)carbamate

HRID 596006Notes

Reaction equation

HRID 596006 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:19][S@@](C(C)(C)C)=O)[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:5]=[C:6]([F:8])[CH:7]=1.Cl>C(Cl)Cl>[NH2:19][C@@H:9]([C:4]1[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([Br:1])[CH:3]=1)[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131734613tert-butyl ((S)-2-(3-bromo-5-fluorophenyl)-2-((R)-1,1-dimethylethylsulfinamido)ethyl)carbamate

Product 1

HCID 118054648(S)-tert-butyl (2-amino-2-(3-bromo-5-fluorophenyl)ethyl)carbamateYield 22.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl ((S)-2-(3-bromo-5-fluorophenyl)-2-((R)-1,1-dimethylethylsulfinamido)ethyl)carbamate (1.78 g, 4.07 mmol) in DCM (13.57 mL) was added HCl (4M in dioxane) (4.07 mL, 16.28 mmol) at room temperature. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was neutralized to pH=7, then extracted by EtOAc to give the desired (S)-tert-butyl (2-amino-2-(3-bromo-5-fluorophenyl)ethyl)carbamate (300 mg) as a free base. LCMS (m/z): 317.1/319.1 (MH+), 0.66 min.

Workup

  1. extractionextracted by EtOAc

Sources & evidence

ORD record
ord-899e2b774c2f412c96bf9a1c46041384
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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