Hydroxylamine → (2R,3S)-N,2-dihydroxy-3-{[4-(4-methoxyphenyl)piperazin-1-yl]carbonyl}-5-methylhexanamide

HRID 888229Notes

Reaction equation

HRID 888229 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C@H:17]([C@H:22]3[O:26]C(C)(C)[O:24][C:23]3=O)[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[NH2:30][OH:31]>CC(O)C>[OH:31][NH:30][C:23](=[O:24])[C@H:22]([OH:26])[C@@H:17]([C:15]([N:12]1[CH2:11][CH2:10][N:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:14][CH2:13]1)=[O:16])[CH2:18][CH:19]([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 58488008HCID 58488008, compound

Product 1

HCID 58487988(2R,3S)-N,2-dihydroxy-3-{[4-(4-methoxyphenyl)piperazin-1-yl]carbonyl}-5-methylhexanamideYield 55%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of (5R)-5-((1S)-1-{[4-(4-methoxyphenyl)piperazin-1-yl]carbonyl}-3-methylbutyl)-2,2-dimethyl-1,3-dioxolan-4-one (108 mg, 0.27 mmol) in iPrOH (4 mL) was added a 50% aqueous solution of hydroxylamine (80 μL) and the resulting mixture was stirred at RT for 2 hours. Then the white solid was filtered off, washed with water and dried under reduced pressure to give 56 mg (55%) of the title compound as a white powder. HPLC, Rt: 1.57 min (purity: 99.1%). LC/MS, M+(ESI): 380.2, M−(ESI): 378.2. 1H NMR (CD3OD, 300 MHz) δ 7.01 (d, J=9.1 Hz, 2H), 6.89 (d, J=9.1 Hz, 2H), 4.05 (d, J=6.8 Hz, 1H), 3.96 (m, 2H), 3.80 (m, 1H), 3.78 (s, 3H), 3.68 (m, 1H), 3.49 (m, 1H), 3.15-2.99 (m, 4H), 1.72 (m, 1H), 1.54 (m, 1H), 1.29 (m, 1H), 0.96 (d, J=6.5 Hz, 3H), 0.95 (d, J=6.4 Hz, 3H).

Workup

  1. filtrationThen the white solid was filtered off
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-e354068df4094afe9a1f685228e10525
Source dataset
uspto-grants-2012_08
Patent number
US08247437B2

Reaction notes

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