Dimethyl Ether → 1-[2-N-[2-(trimethylsilyl)ethoxycarbonyl]pteroyl]-imidazole

HRID 732234Notes

Reaction equation

HRID 732234 reaction equation
C(O)(=O)[C:2]1[CH:21]=[CH:20][C:5]([NH:6][CH2:7][C:8]2[N:19]=[C:18]3[C:11]([N:12]=[C:13]([NH:15][C:16]3=[O:17])[NH2:14])=[N:10][CH:9]=2)=[CH:4][CH:3]=1.C1N=CN([C:29]([N:31]2[CH:35]=[N:34][CH:33]=[CH:32]2)=[O:30])C=1.[CH3:36][Si:37]([CH3:42])([CH3:41])[CH2:38][CH2:39][OH:40].[CH3:43][O:44]C>CS(C)=O.C(O)(=O)C.O.C(N(CC)CC)C>[CH3:36][Si:37]([CH3:42])([CH3:41])[CH2:38][CH2:39][O:40][C:43]([NH:14][C:13]1[NH:15][C:16](=[O:17])[C:18]2[C:11](=[N:10][CH:9]=[C:8]([N:19]=2)[CH2:7][NH:6][C:5]2[CH:4]=[CH:3][C:2]([C:29]([N:31]3[CH:32]=[CH:33][N:34]=[CH:35]3)=[O:30])=[CH:21][CH:20]=2)[N:12]=1)=[O:44]

Participants

9

Reactant 4

HCID 8254Dimethyl EtherHCID 180132-(Trimethylsilyl)ethanolHCID 682631,1'-CarbonyldiimidazoleHCID 135398749Pteroic Acid

Product 1

HCID 1354239971-[2-N-[2-(trimethylsilyl)ethoxycarbonyl]pteroyl]-imidazoleYield 54.8%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 3.0 g of pteroic acid and 5.35 mL of triethylamine (TEA), 6.24 g of CDI as dissolved in 50 mL of DMSO was added and reacted at room temperature for 3.5 hours. To the reaction solution 2-(trimethylsilyl)ethanol (9.63 mL) was added, followed by further 5 hours' reaction at room temperature. The reaction solution was added dropwise into water (10 mL)-acetic acid (0.32 mL) and dimethyl ether (6.4 mL), vigorously stirred for a few minutes, and recovered as solid by suction filtration. The solid product was purified by column chromatography (silica gel column: eluent; 10% methanol in chloroform) and dried under reduced pressure to finally give 2.67 g (yield=54.8%) of aimed compound.

Workup

  1. additionwas added
  2. customreacted at room temperature for 3.5 hours
  3. custom' reaction at room temperature
  4. filtrationrecovered as solid by suction filtration
  5. customThe solid product was purified by column chromatography (silica gel column: eluent; 10% methanol in chloroform)

Sources & evidence

ORD record
ord-42e250f989f147e3b685a9e5f6b782eb
Source dataset
uspto-grants-2009_09
Patent number
US07585973B2

Reaction notes

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