1,2-Dichloroethane → HCID 86757663, compound

HRID 2269359Notes

Reaction equation

HRID 2269359 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C@H:10]([C@H:14]([OH:18])[CH2:15][CH2:16][CH3:17])[C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[O:25][NH2:26].C(Cl)CCl>ClCCl>[O:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[O:25][NH:26][C:11](=[O:13])[C@H:10]([CH2:9][CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C@H:14]([OH:18])[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 57197129HCID 57197129, compound

Product 1

HCID 86757663HCID 86757663, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of (2R,3R)-2-(3-phenyl-1-propyl)-3-hydroxyhexanoic acid (1.53 g, 6.12 mmol) in dichloromethane (6 mL) is added 2-tetrahydropyranyloxyamine (0.93 g, 7.96 mmol) and EDC (1.29 g, 6.73 mmol). The resulting solution is stirred at 23° C. for 3 h, concentrated in vacuo, and diluted with 50 mL of EtOAc. The organic layer is washed sequentially with 1 N hydrochloric acid, saturated aqueous sodium bicarbonate solution, saturated aqueous sodium chloride solution, and is dried over anhydrous magnesium sulfate. Concentration under reduced pressure and purification by silica gel chromatography (elution with 2:1 EtOAc-hexanes) provides (2R,3R)-2-(3-phenyl-1-propyl)-3-hydroxyhexanoic acid 2-tetrahydropyranyloxyamide as a solid (1.62 g, 76% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with 50 mL of EtOAc
  3. washThe organic layer is washed sequentially with 1 N hydrochloric acid, saturated aqueous sodium bicarbonate solution, saturated aqueous sodium chloride solution
  4. dry with materialis dried over anhydrous magnesium sulfate
  5. concentrationConcentration
  6. customunder reduced pressure and purification
  7. washby silica gel chromatography (elution with 2:1 EtOAc-hexanes)

Sources & evidence

ORD record
ord-0061cffa9b6d4bf98cd4d310fa8ca5cd
Source dataset
uspto-grants-2001_12
Patent number
US06329400B1

Reaction notes

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