Benzyl bromoacetate → {(Butane-1-sulfonyl)-[4-(4-oxo-piperidin-1-yl)-phenyl]-amino}-acetic acid benzyl ester

HRID 1061355Notes

Reaction equation

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

Participants

Reactant 2

HCID 62576Benzyl bromoacetate

HCID 86584570N-[4-(4-Oxo-1-piperidinyl)phenyl]-1-butanesulfonamide

Product 1

HCID 69655032{(Butane-1-sulfonyl)-[4-(4-oxo-piperidin-1-yl)-phenyl]-amino}-acetic acid benzyl ester

Procedure

The title compound was prepared from butane-1-sulfonic acid [4-(4-oxo-piperidine-1-yl)-phenyl]-amide (which was obtained in Example 228) and benzyl-2-bromoacetate according to the procedure of Example 251 as an orange oil; 1H NMR (300 MHz, CDCl3) δ 0.91 (t, J=7.29 Hz, 3H), 1.34-1.47 (m, 2H), 1.75-1.86 (m, 2H), 2.55 (t, J=6.09 Hz, 4H), 3.17-3.23 (m, 2H), 3.62 (t, J=6.00 Hz, 4H), 4.45 (s, 2H), 5.18 (s, 2H), 6.87-6.92 (m, 2H), 7.30-7.40 (m, 7H); MS (ES) m/z: 459.0 (MH+); HRMS found for C24H30N2O5S: 459.1944.

Sources & evidence

ORD record: ord-5ec95bd06c354174b30b0aafa7ee5cac
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525202B2

Reaction notes

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