Tetrahydrofuran → HCID 21713926, compound

HRID 649809Notes

Reaction equation

HRID 649809 reaction equation
[CH:1]1([C:7]([N:9]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][C:19]=3[O:27][CH3:28])[CH2:14][CH2:13]2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O1CCCC1.O.NN>[Ni+2].CO>[CH:1]1([C:7]([N:9]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:19]=3[O:27][CH3:28])[CH2:14][CH2:13]2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)2×HCID 21713906HCID 21713906, compound

Product 1

HCID 21713926HCID 21713926, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 934Nickel cationCatalystHCID 887MethanolSolvent

Procedure

A mixture consisting of 1.70 g of compound of Example 5, 18 mL of tetrahydrofurane, 18 mL of methanol, 50 mg of Nichel-Raney and 1 mL of hydrazine hydrate was stirred for 2 h, at room temperature, followed by the addition of 1 mL of hydrazine hydrate, and stirred for 1 h, at a temperature of 50° C. The catalyst was then filtered out, and the recovered solution was evaporated to dryness, affording the crude product, which was then purified by flash chromatography (ethyl acetate—3 N solution of ammonia, in methanol; 95:5). Subsequent evaporation of the solvents afforded 1.33 g of the title compound (yield 84%).

Workup

  1. stirringstirred for 1 h, at a temperature of 50° C
  2. filtrationThe catalyst was then filtered out
  3. customthe recovered solution was evaporated to dryness
  4. customaffording the crude product, which
  5. customwas then purified by flash chromatography (ethyl acetate—3 N solution of ammonia, in methanol; 95:5)
  6. customSubsequent evaporation of the solvents

Sources & evidence

ORD record
ord-c80d7e86fcc24712bb5f89edf95eae72
Source dataset
uspto-grants-2001_08
Patent number
US06271234B1

Reaction notes

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