Hydrochloric Acid → HCID 86601047, compound

HRID 1392966Notes

Reaction equation

HRID 1392966 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16](=[O:24])[CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:12][CH2:11]2)=[N:7][CH:6]=1)=[O:4].Cl.NO.C[O-].[Na+].CO.Cl>O1CCOCC1>[C:18]1([CH2:17][C:16]([N:13]2[CH2:14][CH2:15][N:10]([C:8]3[S:9][C:5]([C:3]([OH:4])=[O:2])=[CH:6][N:7]=3)[CH2:11][CH2:12]2)=[O:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 69201870HCID 69201870, compound

Product 1

HCID 86601047HCID 86601047, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of compound 22c (100 mg, 0.377 mmol) in 1,4-dioxane (2 mL) were added hydroxylamine hydrochloride (208 mg, 3.771 mmol) and a freshly prepared solution of sodium methoxide in methanol (103 mg, 4.471 mmol of sodium dissolved in 1.5 mL of methanol) under a N2 atmosphere. The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was acidified to pH˜6 with 1M HCl and the formed precipitates were filtered off. The filtrate was diluted with ethyl acetate (5 mL) and water (2 mL) and the organic layer was separated. The aqueous layer was washed with ethyl acetate (5 mL) and the combined organic layers were dried on sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC to give 23c. HPLC: Rt=5.62 min.

Workup

  1. customthe formed precipitates
  2. filtrationwere filtered off
  3. additionThe filtrate was diluted with ethyl acetate (5 mL) and water (2 mL)
  4. customthe organic layer was separated
  5. washThe aqueous layer was washed with ethyl acetate (5 mL)
  6. customthe combined organic layers were dried on sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-bdd668607ca34d05841425a06fdca376
Source dataset
uspto-grants-2008_03
Patent number
US07345043B2

Reaction notes

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