Hydrochloric Acid → HCID 57673913, compound

HRID 600198Notes

Reaction equation

HRID 600198 reaction equation
[F:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C@@:17]2([CH2:23][O:24][P:25](=[O:36])([O:31]C(C)(C)C)[O:26]C(C)(C)C)[CH2:21][O:20]C(C)=[N:18]2)=[CH:11][CH:10]=1.Cl>C(O)C>[NH2:18][C@:17]([CH2:21][OH:20])([CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][F:1])=[CH:10][CH:11]=1)[CH2:23][O:24][P:25](=[O:26])([OH:31])[OH:36]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67054594HCID 67054594, compound

Product 1

HCID 57673913HCID 57673913, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of phosphoric acid di-tertbutyl 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.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue is re-dissolved in ethyl acetate
  3. customprecipitated with hexanes
  4. filtrationThe solid is filtered off
  5. washwashed with dry ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-e74c1a4d3b764f7594c897054b3df35f
Source dataset
uspto-grants-2011_03
Patent number
US07902175B2

Reaction notes

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