1,2-Dichloroethane → HCID 53816568, compound

HRID 2269342Notes

Reaction equation

HRID 2269342 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C@H:10]([C@H:14]([OH:16])[CH3:15])[C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[O:23][NH2:24].C(Cl)CCl>ClCCl>[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[O:23][NH:24][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:16])[CH3:15]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 57084727HCID 57084727, compound

Product 1

HCID 53816568HCID 53816568, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
23 °C

Procedure

To a solution of (2R,3R)-2-(3-phenyl-1-propyl)-3-hydroxybutanoic acid (33.0 g, 148.7 mmol) in dichloromethane (300 mL) is added 2-tetrahydropyranyloxyamine (18.3 g, 156.1 mmol) and EDC (31.2 g, 163.5 mmol). The resulting solution is stirred at 23° C. for 16 h, then diluted with dichloromethane (500 mL) and washed sequentially with 1 N hydrochloric acid, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution. The reaction mixture is dried over magnesium sulfate and concentrated under reduced pressure to provide (2R,3R)-2-(3-phenyl-1-propyl)-3-hydroxybutanoic acid 2-tetrahydropyranyloxyamide as a foam (47.8 g, 100% yield).

Workup

  1. washwashed sequentially with 1 N hydrochloric acid, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution
  2. dry with materialThe reaction mixture is dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fca5e8e433c54d5f802aabc92b89e9b8
Source dataset
uspto-grants-2001_12
Patent number
US06329400B1

Reaction notes

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