Benzyl bromoacetate → {(3,4-Dimethoxy-benzenesulfonyl)-[4-(4-oxo-piperidin-1-yl)-phenyl]-amino]-acetic acid benzyl ester

HRID 1061356Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:28]([O:35][C:36](=[O:39])[CH2:37]Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH2:28]([O:35][C:36](=[O:39])[CH2:37][N:14]([S:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:12])=[O:13])[C:15]1[CH:16]=[CH:17][C:18]([N:21]2[CH2:22][CH2:23][C:24](=[O:27])[CH2:25][CH2:26]2)=[CH:19][CH:20]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Reactant 2

HCID 62576Benzyl bromoacetate

HCID 222204173,4-Dimethoxy-N-[4-(4-oxo-piperidin-1-yl)-phenyl]-benzenesulfonamide

Product 1

HCID 69655101{(3,4-Dimethoxy-benzenesulfonyl)-[4-(4-oxo-piperidin-1-yl)-phenyl]-amino]-acetic acid benzyl ester

Procedure

The title compound was prepared from 3,4-dimethoxy-N-[4-(4-oxo-piperidine-1-yl)-phenyl]-benzenesulfonamide (which was obtained in Example 242) and benzyl-2-bromoacetate according to the procedure of Example 251 as an orange gum; 1H NMR (300 MHz, CDCl3) δ 2.53 (t, J=6.06 Hz, 4H), 3.59 (t, J=6.00 Hz, 4H), 3.79 (s, 3H), 3.93 (s, 3H), 4.50 (s, 2H), 5.13 (s, 2H), 6.78-6.87 (m, 2H), 7.07-7.10 (m, 2H), 7.15 (d, J=2.1 Hz, 1H), 7.27-7.37 (m, 7H); MS (ES) m/z: 539.0 (MH+); HRMS found for C28H30N2O7S(MH+): 539.1842.

Sources & evidence

ORD record: ord-ad4eeaf1220a4676bf017e27f809cd1d
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525202B2

Reaction notes

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