Hydrochloric Acid → HCID 58155290, compound

HRID 1929485Notes

Reaction equation

HRID 1929485 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:21])=[C:6]([C@:8]([NH:14][S@](C(C)(C)C)=O)([CH3:13])[C:9]([OH:12])([CH3:11])[CH3:10])[CH:7]=1.Cl>O1CCCC1>[NH2:14][C@@:8]([C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[F:21])([CH3:13])[C:9]([CH3:10])([OH:12])[CH3:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66931424HCID 66931424, compound

Product 1

HCID 58155290HCID 58155290, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-2-methyl-propane-2-sulfinic acid [(R)-1-(5-bromo-2-fluoro-phenyl)-2-hydroxy-1,2-dimethyl-propyl]-amide (4.2 g, 11.04 mmol) in tetrahydrofuran (200 ml) was cooled to 0° C. Hydrochloric acid (4 M in dioxane, 11 ml) was added dropwise. The ice bath was removed and stirring continued for 1.5 hours at room temperature. For the workup, the reaction mixture was poured onto a sodium carbonate solution (2 M), extracted twice with ethyl acetate, dried over sodium sulfate, and evaporated at reduced pressure, finally dried under high vacuum. The (R)-3-amino-3-(5-bromo-2-fluoro-phenyl)-2-methyl-butan-2-ol was obtained as light yellow oil (2.94 g, 96.4% of theory). Mass (calculated) C11H15BrFNO [276.147]; (found) [M+H]+=276, [M+2-H]+=278.

Workup

  1. customThe ice bath was removed
  2. additionFor the workup, the reaction mixture was poured onto a sodium carbonate solution (2 M)
  3. extractionextracted twice with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. customevaporated at reduced pressure
  6. customfinally dried under high vacuum

Sources & evidence

ORD record
ord-66bb4e2ec0974f6ba958095ea4b38629
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

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