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

HRID 1072061Notes

Reaction equation

HRID 1072061 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:12]([O:19][C@H:20]([C@H:22]([N:26]1[CH:30]=[C:29]([C:31]([NH2:33])=[O:32])[N:28]=[CH:27]1)[CH2:23][CH2:24]O)[CH3:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:12]([O:19][C@H:20]([C@H:22]([N:26]1[CH:30]=[C:29]([C:31]([NH2:33])=[O:32])[N:28]=[CH:27]1)[CH2:23][CH2:24][O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH3:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 70051-NaphtholHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 695273111-[(2S,3R)-2-benzyloxy-5-hydroxy-3-pentyl]imidazole-4-carboxamide

Product 1

HCID 696784121-[(2S,3R)-2-benzyloxy-5-(1-naphthyloxy)-3-pentyl]imidazole-4-carboxamideYield 50.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 1-naphthol (48.5 mg, 0.336 mmol), 1-[(2S,3R)-2-benzyloxy-5-hydroxy-3-pentyl]imidazole-4-carboxamide (85 mg, 0.280 mmol), and triphenylphosphine (88.2 mg, 0.336 mmol) in tetrahydrofuran (5 ml) was added dropwise diethyl azodicarboxylate (58.6 mg, 0.336 mmol) at ice-bath temperature. After the mixture was stirred overnight at room temperature, the solvent was removed in vacuo. The residue was purified by silica gel (10 g) chromatography eluting with chloroform/methanol (40:1) to give a mixture (60.6 mg) of 1-[(2S,3R)-2-benzyloxy-5-(1-naphthyloxy)-3-pentyl]imidazole-4-carboxamide (13) 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 (40:1)

Sources & evidence

ORD record
ord-970ebe734d4d4af287d2d7a8e84fa9c0
Source dataset
uspto-grants-2005_06
Patent number
US06908940B2

Reaction notes

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