Hydrochloric Acid → HCID 118659618, compound

HRID 1477243Notes

Reaction equation

HRID 1477243 reaction equation
C(OC([NH:8][C:9]([CH3:36])([CH3:35])[C@H:10]([NH:15][C:16]([C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:28]#[C:29][C@@H:30]3[CH2:32][C@H:31]3[CH2:33][OH:34])[CH:24]=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]([CH3:36])([CH3:35])[C@H:10]([NH:15][C:16]([C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:28]#[C:29][C@@H:30]3[CH2:32][C@H:31]3[CH2:33][OH:34])[CH:24]=2)[CH:19]=1)=[O:17])[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118659432HCID 118659432, compound

Product 1

HCID 118659618HCID 118659618, compoundYield 79%

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)-2-naphthamido)-3-methylbutanoate (64) in methanol (10 mL) was added 4N HCl in dioxane (10 mL) and the reaction mixture was stirred at rt for 2 hr, then at 4° C. overnight. The mixture was concentrated under reduced pressure to give 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)-2-naphthamido)-3-methylbutanoate (6.5, 1.2 g, 3.0 mmol, 79%).

Workup

  1. customat 4° C.
  2. customovernight
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customto give 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-ba0f03a3abb44f8a8dee0838f0c7492c
Source dataset
uspto-grants-2016_08
Patent number
US09403758B2

Reaction notes

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