Water → 5-(2-Adamantan-1-yl-ethyl)-2-o-tolyl-1H-imidazole-4-carboxylic Acid 3-benzyloxycarbonyl-phenyl Ester

HRID 1018376Notes

Reaction equation

HRID 1018376 reaction equation
[C:1]12([CH2:11][CH2:12][C:13]3[NH:17][C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[CH3:24])=[N:15][C:14]=3[C:25]([OH:27])=[O:26])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:40]([O:47][C:48]([C:50]1[CH:51]=[C:52](O)[CH:53]=[CH:54][CH:55]=1)=[O:49])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.O>CN(C=O)C>[CH2:40]([O:47][C:48]([C:50]1[CH:55]=[C:54]([O:26][C:25]([C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH3:24])[NH:17][C:13]=2[CH2:12][CH2:11][C:1]23[CH2:8][CH:7]4[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]4)[CH2:10]2)[CH2:2]3)=[O:27])[CH:53]=[CH:52][CH:51]=1)=[O:49])[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 11736317Benzyl 3-hydroxybenzoateHCID 184053605-(2-Adamantan-1-yl-ethyl)-2-o-tolyl-1H-imidazole-4-carboxylic acid

Product 1

HCID 539858635-(2-Adamantan-1-yl-ethyl)-2-o-tolyl-1H-imidazole-4-carboxylic Acid 3-benzyloxycarbonyl-phenyl EsterYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

A solution of 5-(2-adamantan-1-yl-ethyl)-2-o-tolyl-1H-imidazole-4-carboxylic acid (Example 93) (57 mg, 0.16 mmol) and 1,1′-carbonyldiimidazole(25 mg, 0.16 mmol) in DMF (0.5 ml) was stirred at room temperature for 30 min. 3-Benzyloxycarbonyl-phenol (36 mg, 0.16 mmol) was added and the mixture was stirred at 115° C. for 16 h, then cooled to room temperature. Water (5 ml) was added and the mixture was extracted with ethyl acetate (3×5 ml). The combined extracts were washed with brine, dried (MgSO4) and the solvent was evaporated. The crude product was purified by flash chromatography (silica, DCM/ethyl acetate 9:1) to afford colourless foam (15 mg, 17%). 1H NMR (300 MHz, CDCl3) 7.97 (1H, m), 7.91 (1H, m), 7.39 (4H, m), 5.37 (2H, s), 3.01 (2H, m), 2.52 (3H, s), 1.94 (3H, br s), 1.66 (6H, m), 1.54 (8H, m).

Workup

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate (3×5 ml)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated
  6. customThe crude product was purified by flash chromatography (silica, DCM/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-308da546a0044e44a0cc20d16206a7c3
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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