Ammonia → HCID 57980016, compound

HRID 1867551Notes

Reaction equation

HRID 1867551 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][N:10]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18]O)=[CH:14][CH:13]=3)[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:20]1[CH2:24][C:23](=[O:25])[NH:22][C:21]1=[O:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:46](C(OC(C)C)=O)=NC(OC(C)C)=O.N>O1CCCC1.CO.CC(C)=O>[C:1]1([C:7]2[N:8]=[CH:9][N:10]([C:12]3[CH:13]=[CH:14][C:15]([CH2:18][NH:46][C:21](=[O:26])[O:20][CH2:24][C:23]([NH2:22])=[O:25])=[CH:16][CH:17]=3)[CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

9

Reactant 5

HCID 222AmmoniaHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 973892,4-OxazolidinedioneHCID 54554517HCID 54554517, compound

Product 1

HCID 57980016HCID 57980016, compoundYield 30.6%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.0 g (4 mmol) of [4-(4-phenyl-1H-imidazol-1-yl)phenyl]methanol, prepared in step 12.1., 0.485 g (4.80 mmol) of 1,3-oxazolidine-2,4-dione and 1.15 g (4.38 mmol) of triphenylphosphine in 16 ml of tetrahydrofuran, cooled by a bath of acetone and ice, is admixed dropwise with 0.80 g (4 mmol) of diisopropyl azodicarboxylate in solution in 2 ml of tetrahydrofuran. The mixture is subsequently warmed to ambient temperature again and stirred overnight. 9 ml of the solution are taken, to which are added 12 ml of a 7N ammonia solution (84 mmol) in methanol. The mixture is left to react overnight, admixed with 4 g of silica and evaporated to dryness. The product is purified by chromatography on silica gel, eluting with a 95/5 then 93/7 and 90/10 mixture of dichloromethane and methanol. The product is recrystallized from a mixture of methanol and diisopropyl ether, to give 0.429 g of product in the form of white crystals.

Workup

  1. waitThe mixture is left
  2. customto react overnight
  3. customevaporated to dryness
  4. customThe product is purified by chromatography on silica gel
  5. washeluting with a 95/5
  6. addition93/7 and 90/10 mixture of dichloromethane and methanol
  7. customThe product is recrystallized from a mixture of methanol and diisopropyl ether

Sources & evidence

ORD record
ord-64f9048b327d4659aba5c2f17b8eb530
Source dataset
uspto-grants-2009_12
Patent number
US07632850B2

Reaction notes

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