Acetic Acid → HCID 69288061, compound

HRID 853814Notes

Reaction equation

HRID 853814 reaction equation
[NH2:1][C:2]([CH2:16][OH:17])([CH2:14][OH:15])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:13])[CH3:12])=[CH:7][CH:6]=1.[CH2:18](C(CC)(CC)C([O-])([O-])[O-])[CH3:19].C(O)(=O)C>ClC(Cl)C>[OH:17][CH2:16][C:2]1([CH2:3][CH2:4][C:5]2[CH:10]=[CH:9][C:8]([C:11](=[O:13])[CH3:12])=[CH:7][CH:6]=2)[CH2:14][O:15][C:18]([CH3:19])=[N:1]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 21875354TriethylorthoaceateHCID 69490207HCID 69490207, compound

Product 1

HCID 69288061HCID 69288061, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 1-[4-(3-amino-4-hydroxy-3-hydroxymethyl-butyl)-phenyl]-ethanone (1 mmol) in anhydrous dichloroethane (2 mL) is added triethylorthoacetate (1.1 mmol) and acetic acid (0.05 mmol). The resulting mixture is heated at 80° C. for 12 hours. After concentration, the residue is purified by flash column chromatography (EtOAc) to give 1-{4-[2-(4-hydroxymethyl-2-methyl-4,5-dihydro-oxazol-4-yl)-ethyl]-phenyl}-ethanone as an oil; MS: (ES+): 262.1 (M+1)+.

Workup

  1. concentrationAfter concentration
  2. customthe residue is purified by flash column chromatography (EtOAc)

Sources & evidence

ORD record
ord-0b641bf349c746df8a333cf939f65fac
Source dataset
uspto-grants-2007_08
Patent number
US07256206B2

Reaction notes

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