Reaction #577246

ord-80cc806242774a8da64591023f75a9f5

Reaction equation

CC1=N[C@](CCc2ccc(OCCCCCCF)cc2)(COP(=O)(OC(C)(C)C)OC(C)(C)C)CO1
phosphoric acid di-tert-butyl ester (S)-4-{2-[4-(6-fluoro-hexyloxy)-phenyl]-ethyl}-2-methyl-4,5-dihydro-oxazol-4-ylmethyl ester
Cl
HCl
→
N[C@](CO)(CCc1ccc(OCCCCCCF)cc1)COP(=O)(O)O
phosphoric acid mono-{(S)-2-amino-4-[4-(6-fluoro-hexyloxy)-phenyl]-2-hydroxymethyl-butyl}ester

Reactants

CC1=N[C@](CCc2ccc(OCCCCCCF)cc2)(COP(=O)(OC(C)(C)C)OC(C)(C)C)CO1
phosphoric acid di-tert-butyl ester (S)-4-{2-[4-(6-fluoro-hexyloxy)-phenyl]-ethyl}-2-methyl-4,5-dihydro-oxazol-4-ylmethyl ester
Cl
HCl

Reagents

None

Solvents

CCO
ethanol

Conditions

Temperature
85°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Concentrationconcentrated to dryness
  2. 2
    workup.DISSOLUTIONThe residue is re-dissolved in ethyl acetate
  3. 3
    Otherprecipitated with hexanes
  4. 4
    FiltrationThe solid is filtered off
  5. 5
    Washwashed with dry ether
  6. 6
    Otherdried under vacuum

Procedure

To a solution of phosphoric acid di-tert-butyl ester (S)-4-{2-[4-(6-fluoro-hexyloxy)-phenyl]-ethyl}-2-methyl-4,5-dihydro-oxazol-4-ylmethyl ester (33 mg, 0.050 mmol) in ethanol (2 ml) is added conc. HCl (2 ml). The reaction mixture is stirred at 85° C. for 2 hours, then concentrated to dryness. The residue is re-dissolved in ethyl acetate and precipitated with hexanes. The solid is filtered off, washed with dry ether and dried under vacuum to afford phosphoric acid mono-{(S)-2-amino-4-[4-(6-fluoro-hexyloxy)-phenyl]-2-hydroxymethyl-butyl}ester as a colorless powder.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07528120B2uspto-grants-2009_05