Ammonium Chloride → HCID 69330958, compound

HRID 2370926Notes

Reaction equation

HRID 2370926 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1[N:6]=[CH:7][N:8]([C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C([C:42]([O:44][CH3:45])=[O:43])#N.[NH4+].[Cl-]>C1COCC1>[C:10]([N:8]1[CH:9]=[C:5]([CH:4]([C:42]([O:44][CH3:45])=[O:43])[C:3]([O:2][CH3:1])=[O:29])[N:6]=[CH:7]1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 28660Carbonocyanidic acid, methyl esterHCID 2733832Lithium HexamethyldisilazideHCID 105239671-(triphenylmethyl)-1H-Imidazole-4-acetic acid methyl ester

Product 1

HCID 69330958HCID 69330958, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

3.50 g (9.15 mmol) of the compound from example 12a were dissolved in 50 ml of dry THF and cooled to 0° C. 1.67 g (9.96 mmol) of lithium bis(trimethylsilyl)amide as 20% strength solution in THF were added dropwise to this solution while stirring. The resulting mixture was stirred at 0° C. for 30 min and then 0.86 g (10.07 mol) of methyl cyanoformate was added. The reaction mixture was warmed to RT and stirred for a further 2 h, then poured into 400 ml of saturated aqueous NH4Cl solution and extracted twice with EA. The combined organic phases were washed with water, dried over Na2SO4, filtered and concentrated. Chromatography of the residue on silica gel afforded 1.92 g of the title compound. Repeat chromatography of the resulting mixed fraction afforded a further 40 mg of the desired compound.

Workup

  1. stirringThe resulting mixture was stirred at 0° C. for 30 min
  2. temperatureThe reaction mixture was warmed to RT
  3. stirringstirred for a further 2 h
  4. extractionextracted twice with EA
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-10acd22d26784a7196cc53f345d62d64
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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