Hydroxylamine → HCID 87348653, compound

HRID 535100Notes

Reaction equation

HRID 535100 reaction equation
[CH2:1]([C@:8]12[CH2:16][C@H:12]([C:13](=[O:15])[O:14]1)[C@@H:11]([C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:21][CH2:20]1)=[O:18])[CH2:10][CH2:9]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:31][OH:32]>CO>[CH2:1]([C@@:8]1([OH:14])[CH2:16][C@H:12]([C:13]([NH:31][OH:32])=[O:15])[C@@H:11]([C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:21][CH2:20]2)=[O:18])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 67304651HCID 67304651, compound

Product 1

HCID 87348653HCID 87348653, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of (1S,2S,5S)-5-benzyl-2-[(4-phenylpiperazin-1-yl)carbonyl]-6-oxabicyclo[3.2.1]-octan-7-one (8.0 mg, 0.020 mmol) in anhydrous methanol (1.0 mL, 0.025 mol) at rt was added 1.50 M of hydroxylamine in methanol (0.396 mL). The reaction mixture was stirred at rt for 3 h. The reaction was quenched with saturated aqueous NH4Cl (15 mL), extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by reverse phase HPLC with 5-95% MeCN/H2O (with 0.05% TFA) to give the pure product as a colorless solid (2.3 mg, 26% in yield). MS (ESI): (M+H)+=438.1.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl (15 mL)
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by reverse phase HPLC with 5-95% MeCN/H2O (with 0.05% TFA)

Sources & evidence

ORD record
ord-32184010eaff450b995c48281afadfda
Source dataset
uspto-grants-2014_10
Patent number
US08853243B2

Reaction notes

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