Benzyl bromoacetate → (Butyl-[4-(4-oxo-piperidin-1-yl)-benzenesulfonyl]-amino)-acetic acid benzyl ester

HRID 1278740Notes

Reaction equation

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

Participants

Reactant 2

HCID 62576Benzyl bromoacetate

HCID 12051795N-butyl-4-(4-oxo-piperidin-1-yl)-benzenesulfonamide

Product 1

HCID 69899200(Butyl-[4-(4-oxo-piperidin-1-yl)-benzenesulfonyl]-amino)-acetic acid benzyl ester

Procedure

The title compound was prepared from N-butyl-4-(4-oxo-piperidin-1-yl)-benzenesulfonamide ( ) and benzyl bromoacetate according to the procedure of Intermediate 2 as a gum; 1H NMR (CDCl3) δ 0.85 (t, J=7.23 Hz, 3H), 1.19-1.32 (m, 2H), 1.43-1.53 (m, 2H), 2.56 (t, J=6.12 Hz, 4H), 3.19 (t, J=7.47 Hz, 2H), 3.72 (t, J=6.06 Hz, 4H), 4.09 (s, 2H), 5.10 (s, 2H), 6.84-6.89 (m, 2H), 7.29-7.40 (m, 5H), 7.69-7.74 (m, 2H); MS (ES) m/z 45.94 (MH+); HRMS for C25H30N2O6S: 459.1945 (MH+).

Sources & evidence

ORD record: ord-435e1e9afae6488f81b2b996ff453199
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06444685B1

Reaction notes

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