Acetic Acid → HCID 70162931, compound

HRID 1018375Notes

Reaction equation

HRID 1018375 reaction equation
[C:1]12([CH2:11][CH2:12][C:13]3[N:17]([CH3:18])[C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[CH3:25])=[N:15][C:14]=3[CH:26]=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH2:28]([O:35][C:36](=[O:44])[C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([NH2:43])[CH:38]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)(O)[O-].[Na+]>ClCCCl>[CH2:28]([O:35][C:36](=[O:44])[C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([NH:43][CH2:26][C:14]2[N:15]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:25])[N:17]([CH3:18])[C:13]=2[CH2:12][CH2:11][C:1]23[CH2:10][CH:5]4[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]4)[CH2:8]2)[CH2:2]3)[CH:38]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 15428374Benzyl 3-aminobenzoateHCID 184054185-(2-Adamantan-1-yl-ethyl)-1-methyl-2-o-tolyl-1H-imidazole-4-carbaldehyde

Product 1

HCID 70162931HCID 70162931, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 5-(2-adamantan-1-yl-ethyl)-1-methyl-2-o-tolyl-1H-imidazole-4-carbaldehyde (Example 275, step b) (500 mg, 1.38 mmol) and 3-amino-benzoic acid benzyl ester (313 mg, 1.38 mmol) in 1,2-dichloroethane (5 ml) were added sodium triacetoxyborohydride (409 mg, 1.93 mmol) and then acetic acid (79 μl, 1.38 mmol). The suspension was stirred at room temperature for 2 h, then saturated sodium bicarbonate (40 ml) was added. The product was extracted with ethyl acetate (40 ml), the organic phase was washed with brine (40 ml), dried (MgSO4) and the filtrate was evaporated. The residue was purified by flash column chromatography (silica, hexane/ethyl acetate 1:1) to afford the product (725 mg, 92%). 1H NMR (300 MHz, CDCl3) 7.44-7.23 (12H, m), 6.91 (1H, m), 5.36 (2H, s), 4.50 (1H, br s), 4.24 (2H, s), 3.33 (3H, s), 2.61 (2H, m), 2.20 (3H, s), 2.00 (3H, br s), 1.77-1.57 (12H, m), 1.31 (2H, m).

Workup

  1. extractionThe product was extracted with ethyl acetate (40 ml)
  2. washthe organic phase was washed with brine (40 ml)
  3. dry with materialdried (MgSO4)
  4. customthe filtrate was evaporated
  5. customThe residue was purified by flash column chromatography (silica, hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-64a28131cbcb4ff8adf746ad3ecc2cea
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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