Hydrochloric Acid → (3S,4R)-3-[(R)-1-Phenyl-ethylamino]-tetrahydro-pyran-4-carboxylic acid

HRID 497490Notes

Reaction equation

HRID 497490 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][O:9][CH2:8][C@H:7]1[NH:12][C@@H:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14])=[O:5])C.[OH-].[Na+].Cl>O1CCCC1>[C:15]1([C@H:13]([NH:12][C@H:7]2[C@H:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10][O:9][CH2:8]2)[CH3:14])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59042167(3S,4R)-3-[(R)-1-Phenyl-ethylamino]-tetrahydro-pyran-4-carboxylic acid ethyl ester

Product 1

HCID 59042160(3S,4R)-3-[(R)-1-Phenyl-ethylamino]-tetrahydro-pyran-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3S,4R)-3-[(R)-1-Phenyl-ethylamino]-tetrahydro-pyran-4-carboxylic acid ethyl ester (726 mg, 2.6 mmol) in tetrahydrofuran (6 mL) was treated with 1.0 M sodium hydroxide solution (5.2 mL, 5.2 mmol) and the heterogeneous mixture was stirred at room temperature. After 16 h, the now homogeneous solution was treated with 1.0 M hydrochloric acid (5.2 mL, 5.2 mmol) and concentrated in vacuo. The residue was dissolved in water and lyophilized to provide the product, along with sodium chloride, as a fluffy white solid (943 mg, quantitative), used without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water
  3. customto provide the product
  4. customalong with sodium chloride, as a fluffy white solid (943 mg, quantitative), used without further purification

Sources & evidence

ORD record
ord-c544527bcb554dba908a4f5d94691276
Source dataset
uspto-grants-2005_09
Patent number
US06949546B2

Reaction notes

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