Ethanol → HCID 136355249, compound

HRID 271516Notes

Reaction equation

HRID 271516 reaction equation
N1(C[C:8]2[C:9]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[C:24](=O)[CH2:23][CH2:22]4)=[C:10]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[O:11][CH:12]=2)CCOCC1.[NH2:29][OH:30].[CH2:31]([OH:33])[CH3:32]>>[N:16]1([CH2:17][C:12]2[O:11][C:10]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[C:9]([C:19]3[CH:27]=[C:26]4[C:23](=[CH:24][CH:20]=3)[C:22](=[N:29][OH:30])[CH2:21][CH2:25]4)[CH:8]=2)[CH2:15][CH2:14][O:33][CH2:31][CH2:32]1

Participants

4

Reactant 3

HCID 702EthanolHCID 787HydroxylamineHCID 69317410HCID 69317410, compound

Product 1

HCID 136355249HCID 136355249, compoundYield 64%

Procedure

The product of Step 2 (180 mg, 0.4 mmol) in ethanol (4 ml) containing aqueous hydroxylamine (2 ml, 50% in water) was heated under reflux for 1 hour. After cooling to room temperature, the mixture was concentrated in vacuo and the residue co-evaporated with ethanol (3×5 ml). The residue was purified by silica gel chromatography eluting with a 0.1:1:20 mixture of 0.880 ammonia solution:ethanol:chloroform to give the title compound (100 mg, 64%); MS(ES+) m/e 390 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. concentrationthe mixture was concentrated in vacuo
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with a 0.1:1:20 mixture of 0.880 ammonia solution

Sources & evidence

ORD record
ord-3c3dc43f706b4eb6b4f1359922962fb8
Source dataset
uspto-grants-2008_11
Patent number
US07452906B2

Reaction notes

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