Hydroxylamine → HCID 11648223, compound

HRID 1677797Notes

Reaction equation

HRID 1677797 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:19][CH2:18][N:17]([C:20]([C@H:22]([C@@H:27]4[O:31]C(C)(C)O[C:28]4=[O:34])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:21])[C@H:16]([CH3:35])[CH2:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[NH2:36][OH:37]>CC(O)C.C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:19][CH2:18][N:17]([C:20]([C@@H:22]([CH2:23][CH:24]([CH3:26])[CH3:25])[C@H:27]([OH:31])[C:28]([NH:36][OH:37])=[O:34])=[O:21])[C@H:16]([CH3:35])[CH2:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 58487969HCID 58487969, compound

Product 1

HCID 11648223HCID 11648223, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (5S)-5-((1S)-1-{[(2R)-4-(4′-fluorobiphenyl-4-yl)-2-methylpiperazin-1-yl]carbonyl}-3-methylbutyl)-2,2-dimethyl-1,3-dioxolan-4-one (230 mg, 0.48 mmol, 1.0 eq) in a mixture of iPrOH (4 mL) and THF (4 mL) was added a 50% aq. solution hydroxylamine (0.08 mL, 1.43 mmol, 3.0 eq). The reaction mixture was stirred at rt for 8 h. Evaporation of the solvent gave a white solid. This product was washed with iPr2O (2×), filtered and dried under vacuum to give the title compound as a white powder (89%). M−(ESI): 456.3; M+(ESI): 458.4. HPLC (Condition A), Rt: 3.9 min (HPLC purity: 97.5%).

Workup

  1. customEvaporation of the solvent
  2. customgave a white solid
  3. washThis product was washed with iPr2O (2×)
  4. filtrationfiltered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-814a489872fd42d0a0fa12c0f868be7c
Source dataset
uspto-grants-2011_08
Patent number
US08008302B2

Reaction notes

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