Toluene → N-{(1S)-2-[4-(6-hydroxy-1,3-benzoxazol-2-yl)phenoxy]-1-methylethyl}acetamide

HRID 1026215Notes

Reaction equation

HRID 1026215 reaction equation
[C:1]([NH:4][C@@H:5]([CH3:25])[CH2:6][O:7][C:8]1[CH:24]=[CH:23][C:11]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=2[OH:22])=O)=[CH:10][CH:9]=1)(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[OH:21][C:18]1[CH:19]=[CH:20][C:15]2[N:14]=[C:12]([C:11]3[CH:23]=[CH:24][C:8]([O:7][CH2:6][C@@H:5]([NH:4][C:1](=[O:3])[CH3:2])[CH3:25])=[CH:9][CH:10]=3)[O:22][C:16]=2[CH:17]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 677777224-{[(2S)-2-(acetylamino)propyl]oxy}-N-(2,4-dihydroxyphenyl)benzamide

Product 1

HCID 67778241N-{(1S)-2-[4-(6-hydroxy-1,3-benzoxazol-2-yl)phenoxy]-1-methylethyl}acetamideYield 54.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-{[(2S)-2-(acetylamino)propyl]oxy}-N-(2,4-dihydroxyphenyl)benzamide (628 mg) and triphenylphosphine (716 mg) in THF (6.0 mL) was added dropwise a toluene solution (2.2 M, 1.24 mL) of diethyl azodicarboxylate, and the mixture was stirred under a nitrogen atmosphere at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/methanol) to give the title compound (326 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (NH, ethyl acetate/methanol)

Sources & evidence

ORD record
ord-cd8eaaa16e78452d9da037cfee17ba4b
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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