HCID 11983701, compound → HCID 11984190, compound

HRID 490072Notes

Reaction equation

HRID 490072 reaction equation
C(OC([N:8]1[C@:12]([CH2:32][O:33][P:34]([O:41]C(C)(C)C)([O:36]C(C)(C)C)=[O:35])([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][O:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)=[CH:17][CH:16]=2)[CH2:11][O:10]C1(C)C)=O)(C)(C)C>Cl>[NH2:8][C@@:12]([CH2:11][OH:10])([CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH2:23][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)=[CH:19][CH:20]=1)[CH2:32][O:33][P:34](=[O:35])([OH:36])[OH:41]

Participants

3

Reactant 1

HCID 11983701HCID 11983701, compound

Product 1

HCID 11984190HCID 11984190, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Finally, a solution of (R)-4-(di-tert-butoxy-phosphoryloxymethyl)-4-(2-{4-[2-(3-fluoro-phenoxy)-ethoxy]-phenyl}-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (70 mg, 0.10 mmol) in conc. HCl (2 ml). is stirred at room temperature for one hour and is then heated to 95° 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 in vacuo to afford phosphoric acid mono-((R)-2-amino-4-{4-[2-(3-fluoro-phenoxy)-ethoxy]-phenyl}-2-hydroxymethyl-butyl)ester as a colorless powder.

Workup

  1. temperatureis then heated to 95° C. for 2 hours
  2. concentrationconcentrated to dryness
  3. dissolutionThe residue is re-dissolved in ethyl acetate
  4. customprecipitated with hexanes
  5. filtrationThe solid is filtered off
  6. washwashed with dry ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-8256a3c29fc64048b39f33a0abfc157d
Source dataset
uspto-grants-2009_05
Patent number
US07528120B2

Reaction notes

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