(+)-Norepinephrine → HCID 69654609, compound

HRID 1061367Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH:26]1[C:31]([C@H:32]([OH:35])[CH2:33][NH2:34])=[CH:30][C:29]([OH:36])=[C:28]([OH:37])[CH:27]=1>>[OH:36][C:29]1[CH:30]=[C:31]([C@@H:32]([OH:35])[CH2:33][NH:34][CH:22]2[CH2:23][CH2:24][N:19]([C:16]3[CH:15]=[CH:14][C:13]([NH:12][S:9]([C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)(=[O:10])=[O:11])=[CH:18][CH:17]=3)[CH2:20][CH2:21]2)[CH:26]=[CH:27][C:28]=1[OH:37]

Participants

Reactant 2

HCID 5814(+)-Norepinephrine

HCID 222205564-Methoxy-N-[4-(4-oxo-piperidin-1-yl)-phenyl]benzenesulfonamide

Product 1

HCID 69654609HCID 69654609, compound

Procedure

The title compound was prepared from 4-methoxy-N-[4-(4-oxo-piperidine-1-yl)-phenyl]-benzenesulfonamide (which was obtained in Example 218) and L-norepinephrine according to the procedure of Example 255 as a white solid; 1 H NMR (300 MHz, DMSO-d6) δ 1.40-1.55 (m, 2H), 1.90-2.05 (m, 2H), 2.50-3.00 (m, 5H), 3.50-3.75 (m, 2H), 3.79 (s, 3H), 4.50-4.65 (m, 1H), 6.60 (d, J=8.0 Hz, 1H), 6.68 (d, J=8.0 Hz, 1H), 6.76-6.80 (m, 3H), 6.88 (d, J=9.0 Hz, 2H), 7.04 (d, J=7.8 Hz, 2H), 7.61 (d, J=7.8 Hz, 2H), 8.85 (s, 1H); MS (ES) m/z: 513.9 (MH+); HRMS Calcd. for C26H32N3O6S(MH+): 514.2011. Found: 514.2000.

Sources & evidence

ORD record: ord-f8bea31ea6d5419189f47dceac7963ad
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525202B2

Reaction notes

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