Diisopropylethylamine → HCID 19036237, compound

HRID 53010Notes

Reaction equation

HRID 53010 reaction equation
C(N(C(C)C)CC)(C)C.[CH3:10][S:11]([O:14]S(C)(=O)=O)(=[O:13])=[O:12].O[CH2:20][C:21]1[N:22]([CH2:35][C:36]2[CH:41]=[CH:40][C:39]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=3[C:48]3[N:52]([C:53]([C:66]4[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=4)([C:60]4[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=4)[C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=4)[N:51]=[N:50][N:49]=3)=[CH:38][CH:37]=2)[C:23]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:24]([C:26]([OH:29])([CH3:28])[CH3:27])[N:25]=1.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[OH:29][C:26]([C:24]1[N:25]=[C:21]([CH2:20][O:14][S:11]([CH3:10])(=[O:13])=[O:12])[N:22]([CH2:35][C:36]2[CH:37]=[CH:38][C:39]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=3[C:48]3[N:52]([C:53]([C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=4)([C:66]4[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=4)[C:60]4[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=4)[N:51]=[N:50][N:49]=3)=[CH:40][CH:41]=2)[C:23]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31])([CH3:28])[CH3:27]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 19036262HCID 19036262, compound

Product 1

HCID 19036237HCID 19036237, compoundYield 109.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.371 ml of N,N-diisopropyl-N-ethylamine and then 0.371 g of methanesulfonic anhydride were added, under a nitrogen atmosphere, to a solution of 500 mg of ethyl 2-hydroxymethyl-4-(1-hydroxy-1-methylethyl)-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate [prepared as described in step (b) above] in 10 ml of tetrahydrofuran. The mixture was then stirred at room temperature for 1.5 hours, after which it was mixed with ethyl acetate and an aqueous solution of sodium hydrogencarbonate. The ethyl acetate layer was separated, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure, to give 610 mg of the title compound as an amorphous powder. The compound was employed in the subsequent reactions without any further purification.

Workup

  1. customThe ethyl acetate layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-238a6cdea5de4d23b0ad8eed4e73c206
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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