3,4-Dichlorophenol → 1-[(2S,3R)-2-benzyloxy-5-(3,4-dichlorophenoxy)-3-pentyl]imidazole-4-carboxamide

HRID 1829803Notes

Reaction equation

HRID 1829803 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:10]([O:17][C@H:18]([C@H:20]([N:24]1[CH:28]=[C:27]([C:29]([NH2:31])=[O:30])[N:26]=[CH:25]1)[CH2:21][CH2:22]O)[CH3:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:10]([O:17][C@H:18]([C@H:20]([N:24]1[CH:28]=[C:27]([C:29]([NH2:31])=[O:30])[N:26]=[CH:25]1)[CH2:21][CH2:22][O:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[CH3:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 72583,4-DichlorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 695273111-[(2S,3R)-2-benzyloxy-5-hydroxy-3-pentyl]imidazole-4-carboxamide

Product 1

HCID 101609361-[(2S,3R)-2-benzyloxy-5-(3,4-dichlorophenoxy)-3-pentyl]imidazole-4-carboxamideYield 102%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 3,4-dichlorophenol (129 mg, 0.791 mmol), 1-[(2S,3R)-2-benzyloxy-5-hydroxy-3-pentyl]imidazole-4-carboxamide (80 mg, 0.264 mmol), and triphenylphosphine (90 mg, 0.343 mmol) in tetrahydrofuran (5 ml) was added dropwise diethyl azodicarboxylate (59.7 mg, 0.343 mmol) at ice-bath temperature. After the mixture was stirred for 2 h at room temperature, the solvent was removed in vacuo. The residue was purified by silica gel (10 g) chromatography eluting with chloroform/methanol (100:1 to 30:1) to give a mixture (120.6 mg, 102%) of 1-[(2S,3R)-2-benzyloxy-5-(3,4-dichlorophenoxy)-3-pentyl]imidazole-4-carboxamide (3) and by-products. This material was used without further purification.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by silica gel (10 g) chromatography
  3. washeluting with chloroform/methanol (100:1 to 30:1)

Sources & evidence

ORD record
ord-dc2d7060331c4b4caa6ef2be32a7f126
Source dataset
uspto-grants-2006_06
Patent number
US07064144B2

Reaction notes

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