HCID 22618814, compound → HCID 54250094, compound

HRID 842270Notes

Reaction equation

HRID 842270 reaction equation
[NH2:1][C:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH2:5][CH2:6][CH3:7])[CH2:3][OH:4]>C(Cl)Cl.C(N(CC)CC)C.C(Cl)(=O)C>[C:3]([O:4][CH2:3][C:2]([NH:1][C:11](=[O:16])[CH3:10])([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:5][CH2:6][CH3:7])(=[O:4])[CH3:2]

Participants

5

Reactant 1

HCID 22618814HCID 22618814, compound

Product 1

HCID 54250094HCID 54250094, compoundYield 129%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6367Acetyl chlorideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-amino-2-(2-(2-benzyloxyphenyl)ethyl)pentanol (1.1 g) in methylene chloride (35 ml), triethylamine (1.2 ml) and acetyl chloride (0.5 ml) were added and the mixture was stirred at room temperature for 6 hours. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with a dilute hydrochloric acid, an aqueous sodium hydrogencarbonate solution and a saturated brine and dried over magnesium sulfate. The solvent was distilled away under reduced pressure and the residue was subjected to silica gel chromatography (eluent; hexane-ethyl acetate=1:1) to give the subject compound (0.90 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a dilute hydrochloric acid
  3. dry with materialan aqueous sodium hydrogencarbonate solution and a saturated brine and dried over magnesium sulfate
  4. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-b5b64e7934bf43b3a69d9de64f80c0c4
Source dataset
uspto-grants-2002_04
Patent number
US06372800B1

Reaction notes

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