Acetic Acid → HCID 73753167, compound

HRID 618353Notes

Reaction equation

HRID 618353 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:15][CH:14]=2)=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].Cl.[NH2:27][OH:28].C(N(CC)CC)C.CC(O)=O>CCO.CCOC(C)=O.CCCCCC>[NH2:2][C:1](=[N:27][OH:28])[C:3]1[CH:4]=[C:5]([C:9]([NH:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:18]=2)=[O:10])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8471Triethylamine2×HCID 443297Hydroxyamine hydrochloride2×HCID 21191451HCID 21191451, compound

Product 1

HCID 73753167HCID 73753167, compoundYield 102%

Reagents, catalysts & solvents 2

HCID 21226206Ethyl acetate hexaneCatalystHCID 702EthanolSolvent

Conditions

Temperature
88 °C

Procedure

A solution of the compound of Example 12 (0.476 g, 1.3 mmol), hydroxylamine hydrochloride (0.089 g, 1.3 mmol), and triethylamine (0.18 mL, 1.3 mmol) in absolute EtOH (10 mL) was heated to reflux (86-90° C.). After 5 hours, TLC [1:1 EtOAc/hexane (10 mL)+5 drops of AcOH] showed that starting material was still present. Additional hydroxylamine hydrochloride (0.04 g, 0.6 equivalent) and triethylamine (0.09 mL) was added. After 40 minutes, the TLC showed no change. The reaction was concentrated in vacuo and the residue was dissolved in H2O (30 mL). The aqueous layer was extracted with EtOAc (40 mL). The organic layer was collected, dried over MgSO4, and concentrated in vacuo to give a white solid (0.49 g). NMR was consistent with the proposed structure.

Workup

  1. waitAfter 40 minutes
  2. concentrationThe reaction was concentrated in vacuo
  3. dissolutionthe residue was dissolved in H2O (30 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (40 mL)
  5. customThe organic layer was collected
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-64154d591ee3492ba40681414be2944b
Source dataset
uspto-grants-1999_09
Patent number
US05952381

Reaction notes

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