Hydrochloric Acid → HCID 118045772, compound

HRID 596008Notes

Reaction equation

HRID 596008 reaction equation
[NH2:1][CH2:2][C@@H:3]([NH:12][S@](C(C)(C)C)=O)[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([Br:11])[CH:5]=1.N1C=CC=CC=1.[C:25](OC(=O)C)(=[O:27])[CH3:26].Cl>C(Cl)Cl>[NH2:12][C@@H:3]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([Br:11])[CH:5]=1)[CH2:2][NH:1][C:25](=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 118045232HCID 118045232, compound

Product 1

HCID 118045772HCID 118045772, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)—N—((S)-2-amino-1-(3-bromo-5-fluorophenyl)ethyl)-2-methylpropane-2-sulfinamide (100 mg, 0.297 mmol) was dissolved in DCM (988 μl), followed by pyridine (71.9 μl, 0.890 mmol) and acetic anhydride (28.0 μl, 0.297 mmol). The reaction mixture was stirred at room temperature for 1 h, extracted by EtOAc, washed by water and brine, dried over Na2SO4and concentrated. The residue was dissolved in Et2O (1 mL), then HCl (4 M in dioxane) (148 μl, 0.593 mmol) was added. The reaction mixture was stirred at room temperature for 30 min. After the solvent was decant out, the residue solid was used in next step reaction without purification. LCMS (m/z): 275.1/277.1 (MH+), 0.41 min.

Workup

  1. extractionextracted by EtOAc
  2. washwashed by water and brine
  3. customdried over Na2SO4and
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in Et2O (1 mL)
  6. stirringThe reaction mixture was stirred at room temperature for 30 min
  7. customAfter the solvent was decant out
  8. customthe residue solid was used in next step reaction without purification
  9. custom275.1/277.1 (MH+), 0.41 min.

Sources & evidence

ORD record
ord-21fc5f6c10684025a806b5074fef48b3
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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