Water → HCID 53814568, compound

HRID 842281Notes

Reaction equation

HRID 842281 reaction equation
[C:1]([NH:4][CH:5]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)[CH2:6][OH:7])(=[O:3])[CH3:2].[OH2:24].N1[CH:30]=[CH:29]C=CC=1>C(OC(=O)C)(=O)C>[C:29]([O:7][CH2:6][CH:5]([NH:4][C:1](=[O:3])[CH3:2])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)(=[O:24])[CH3:30]

Participants

5

Reactant 3

HCID 962WaterHCID 1049PyridineHCID 22618850HCID 22618850, compound

Product 1

HCID 53814568HCID 53814568, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of 2-acetamido-4-(4-benzyloxyphenyl)butanol (9.48 g) in pyridine (100 ml), acetic anhydride (22.2 ml) was added and the mixture was stirred at room temperature for 5 hours. Then, the solution was poured into water and extracted with ethyl acetate. The extract was washed with a dilute hydrochloric acid, a dilute aqueous sodium hydrogencarbonate solution and a saturated brine, dried over magnesium sulfate and the solvent was distilled away under reduced pressure. The residue obtained was crystallized from ethyl acetate-hexane to give the subject compound (8.32 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with a dilute hydrochloric acid
  3. dry with materiala dilute aqueous sodium hydrogencarbonate solution and a saturated brine, dried over magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe residue obtained
  6. customwas crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-47465d454bb7419c883d4897791e0106
Source dataset
uspto-grants-2002_04
Patent number
US06372800B1

Reaction notes

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