Hydrochloric Acid → HCID 86601046, compound

HRID 1392965Notes

Reaction equation

HRID 1392965 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:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[N:7][CH:6]=1)=[O:4].Cl.NO.C[O-].[Na+].CO.Cl>O1CCOCC1>[C:16]([N:13]1[CH2:14][CH2:15][N:10]([C:8]2[S:9][C:5]([C:3]([OH:4])=[O:2])=[CH:6][N:7]=2)[CH2:11][CH2:12]1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 69199219HCID 69199219, compound

Product 1

HCID 86601046HCID 86601046, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of compound 22b (100 mg, 0.321 mmol) in 1,4-dioxane (2 mL) were added hydroxylamine hydrochloride (222 mg, 3.191 mmol) and a freshly prepared solution of sodium methoxide in methanol (110 mg, 4.712 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 23b. HPLC: Rt=3.69 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-e0e0826ce86c4897ad4c1617901a79ae
Source dataset
uspto-grants-2008_03
Patent number
US07345043B2

Reaction notes

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