Hydroxylamine → HCID 9879575, compound

HRID 1186690Notes

Reaction equation

HRID 1186690 reaction equation
[CH2:1]([NH:8][S:9]([C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[C:14](OC)=[O:15])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:22][OH:23].[OH-].[K+]>C1COCC1.CO.CCOCC>[CH2:1]([NH:8][S:9]([C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[C:14]([NH:22][OH:23])=[O:15])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 787HydroxylamineHCID 14797Potassium HydroxideHCID 58121065HCID 58121065, compound

Product 1

HCID 9879575HCID 9879575, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a 50 mL round-bottomed flask was added methyl 2-(N-benzylsulfamoyl)benzoate 43 (49 mg, 0.160 mmol) in THF (321 μl) and MeOH (321 μl) and the solution was cooled to 0° C. Then, a 50% aqueous solution of hydroxylamine (530 mg, 8.02 mmol) was added, followed by a 4M aqueous solution of KOH (80 μl, 0.321 mmol) and the resulting colorless solution was stirred at 0° C., allowing to slowly warm to rt and stirred for 18 h. The reaction mixture was partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc and combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to provide a colorless oil. A solid was obtained by successive dissolution in Et2O/Hex mixture and concentration which was triturated in Et2O to afford title compound 44 (18 mgs, 37% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 11.25 (s, 1H), 9.34 (s, 1H), 7.83 (dd, J=7.6, 1.2 Hz, 1H), 7.67 (td, J=7.4, 1.4 Hz, 1H), 7.61 (td, J=7.6, 1.6 Hz, 1H), 7.50 (dd, J=7.4, 1.6 Hz, 1H), 7.49 (bs, 1H), 7.27-7.18 (m, 5H), 4.05 (d, J=5.9 Hz, 2H). LRMS (ESI): (calc.) 306.34 (found) 307.14 (MH)+

Workup

  1. temperatureto slowly warm to rt
  2. stirringstirred for 18 h
  3. customThe reaction mixture was partitioned between EtOAc and H2O
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washwere washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto provide a colorless oil
  10. concentrationHex mixture and concentration which
  11. customwas triturated in Et2O

Sources & evidence

ORD record
ord-72631cfe78b44731a90bd5658dfd03e5
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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