Sodium ethoxide → HCID 19036262, compound

HRID 53009Notes

Reaction equation

HRID 53009 reaction equation
[O-]CC.[Na+].C([O:8][CH2:9][C:10]1[N:11]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[C:37]3[N:41]([C:42]([C:55]4[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=4)([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[N:40]=[N:39][N:38]=3)=[CH:27][CH:26]=2)[C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:13]([C:15]([OH:18])([CH3:17])[CH3:16])[N:14]=1)(=O)C>C(O)C>[OH:8][CH2:9][C:10]1[N:11]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[C:37]3[N:41]([C:42]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)([C:55]4[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=4)[C:49]4[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=4)[N:40]=[N:39][N:38]=3)=[CH:29][CH:30]=2)[C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:13]([C:15]([OH:18])([CH3:16])[CH3:17])[N:14]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 19036200HCID 19036200, compound

Product 1

HCID 19036262HCID 19036262, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

0.75 ml of a 0.15N solution of sodium ethoxide in ethanol was added to a solution of 1.69 g of ethyl 2-acetoxymethyl-4-(1-hydroxy-1-methylethyl)-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate [prepared as described in Example 102(a)] in 15 ml of ethanol, and the mixture was stirred at room temperature for 5 minutes. The reaction solution was then concentrated by evaporation under reduced pressure, ethyl acetate and water were added to the residue, and the ethyl acetate layer was separated. This ethyl acetate layer was washed with an aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate, after which it was concentrated by evaporation under reduced pressure. The resulting residue was purified by recrystallization from a mixture of diethyl ether and diisopropyl ether, to give 1.47 g of the title compound as crystals, melting at 151°-152° C.

Workup

  1. concentrationThe reaction solution was then concentrated by evaporation under reduced pressure, ethyl acetate and water
  2. additionwere added to the residue
  3. customthe ethyl acetate layer was separated
  4. washThis ethyl acetate layer was washed with an aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationafter which it was concentrated by evaporation under reduced pressure
  7. customThe resulting residue was purified by recrystallization from a mixture of diethyl ether and diisopropyl ether

Sources & evidence

ORD record
ord-88b6f19ea8c042c39c2d6b6b3e564a0c
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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