Benzyl Alcohol → HCID 57072059, compound

HRID 1018322Notes

Reaction equation

HRID 1018322 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]([CH2:13][CH2:14][C:15]23[CH2:24][CH:19]4[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]4)[CH2:16]2)[CH2:22]3)=[C:11](C(O)=O)[N:10]=[C:9]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:35]=[C:36]=[O:37].[CH2:38]([OH:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>>[C:1]([O:5][C:6]([N:8]1[C:12]([CH2:13][CH2:14][C:15]23[CH2:22][CH:21]4[CH2:20][CH:19]([CH2:18][CH:17]([CH2:23]4)[CH2:16]2)[CH2:24]3)=[C:11]([NH:35][C:36]([O:45][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:37])[N:10]=[C:9]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 244Benzyl Alcohol2×HCID 105034IsocyanateHCID 54458980HCID 54458980, compound

Product 1

HCID 57072059HCID 57072059, compound

Procedure

5-(2-Adamantan-1-yl-ethyl)-2-o-tolyl-imidazole-1,4-dicarboxylic acid 1-tert-butyl ester (Example 75, step c) was converted to the isocyanate and reacted with benzyl alcohol according to the procedure of Example 75, step d using benzyl alcohol in place of 3-amino-benzoic acid benzyl ester. The crude reaction mixture was purified by flash column chromatography (silica, hexane/ethyl acetate 3:2) to give the product. 1H NMR (300 MHz, CDCl3) 7.39-7.19 (9H, m), 6.10 (1H, br s), 5.20 (2H, s), 2.79 (2H, m), 2.18 (3H, s), 1.96 (3H, s), 1.68 (6H, m), 1.50 (6H, s), 1.31 (2H, m), 1.19 (9H, s).

Workup

  1. customThe crude reaction mixture
  2. customwas purified by flash column chromatography (silica, hexane/ethyl acetate 3:2)
  3. customto give the product

Sources & evidence

ORD record
ord-8b12d1b42acd4434b9ced165008f3d67
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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