O-Cresol → HCID 57563711, compound

HRID 507778Notes

Reaction equation

HRID 507778 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][C:8]=1[C:15](=[O:28])[NH:16][CH2:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)[CH3:2].[CH3:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][O:14][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[CH3:30])=[CH:9][C:8]=1[C:15](=[O:28])[NH:16][CH2:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)[CH3:2]

Participants

6

Reactant 4

HCID 335O-CresolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 57563667HCID 57563667, compound

Product 1

HCID 57563711HCID 57563711, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of the compound prepared in Example 4 (300 mg) and 2-methylphenol (0.12 ml) in tetrahydrofuran (4 ml) were added triphenylphosphine (300 mg) and diethyl azodicarboxylate (0.5 ml, 40% toluene solution) at room temperature and the mixture was stirred overnight. The reaction mixture was concentrated and the residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1) to give the title compound (330 mg) having the following physical data.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-c4603fba9b98400badf14c8f0ba70192
Source dataset
uspto-grants-2010_08
Patent number
US07786161B2

Reaction notes

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