Hydrochloric Acid → HCID 118659447, compound

HRID 1477246Notes

Reaction equation

HRID 1477246 reaction equation
C(OC([NH:8][C:9]([CH3:35])([CH3:34])[C@H:10]([NH:15][C:16]([C:18]1[S:22][C:21]2[CH:23]=[C:24]([C:27]#[C:28][C@@H:29]3[CH2:31][C@H:30]3[CH2:32][OH:33])[CH:25]=[CH:26][C:20]=2[CH:19]=1)=[O:17])[C:11]([O:13][CH3:14])=[O:12])=O)(C)(C)C.Cl>CO.O1CCOCC1>[NH2:8][C:9]([CH3:35])([CH3:34])[C@H:10]([NH:15][C:16]([C:18]1[S:22][C:21]2[CH:23]=[C:24]([C:27]#[C:28][C@@H:29]3[CH2:31][C@H:30]3[CH2:32][OH:33])[CH:25]=[CH:26][C:20]=2[CH:19]=1)=[O:17])[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118659501HCID 118659501, compound

Product 1

HCID 118659447HCID 118659447, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirring solution of (S)-methyl 3-((tert-butoxycarbonyl)amino)-2-(6-(((trans)-2-(hydroxymethyl)cyclopropyl)ethynyl)benzo[b]thiophene-2-carboxamido)-3-methylbutanoate (7.3) in methanol (10 mL) was added 4N HCl in dioxane (10 mL) and the reaction was stirred at room temperature for 2 hr, then at 4° C. overnight. The reaction mixture was concentrated under reduced pressure to yield a residue, which was partitioned between water and MTBE. The aqueous layer was basified with saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give (S)-methyl 3-amino-2-(6-(((trans)-2-(hydroxymethyl)cyclopropyl)ethynyl)benzo[b]thiophene-2-carboxamido)-3-methylbutanoate (7.4, 880 mg, 2.2 mmol, 67%).

Workup

  1. customat 4° C.
  2. customovernight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customto yield a residue, which
  5. customwas partitioned between water and MTBE
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with saturated sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-022afaadd2d345b28dd464c3a84772b6
Source dataset
uspto-grants-2016_08
Patent number
US09403758B2

Reaction notes

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