Ethyl chloroformate → HCID 15698064, compound

HRID 653899Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]([OH:23])=[O:22])=[CH:11][CH:10]=2)[C:6]([CH2:24][CH2:25][CH2:26][CH3:27])=[N:5][C:4]=1[Cl:28].Cl[C:30]([O:32][CH2:33][CH3:34])=[O:31]>>[CH2:24]([C:6]1[N:7]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]([OH:23])=[O:22])=[CH:13][CH:14]=2)[C:3]([CH2:2][NH:1][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:4]([Cl:28])[N:5]=1)[CH2:25][CH2:26][CH3:27]

Participants

Reactant 2

HCID 10928Ethyl chloroformate

HCID 15698063HCID 15698063, compound

Product 1

HCID 15698064HCID 15698064, compound

Procedure

2-Butyl-1-[(2'-carboxybiphenyl-4-yl)methyl]-4-chloro-5-(ethoxycarbonylaminomethyl)imidazole was prepared from 5-aminomethyl-2-n-butyl-1-[(2'-carboxybiphenyl-4-yl)methyl]-4-chloroimidazole using ethyl chloroformate and the Schotten-Baumann procedure described in Example 209, Part B: m.p. 144.0°-147.0°. NMR (200 MHz, DMSO-d6) δ 12.74 (s, 1H); 7.73 (d, 1H, J=7Hz); 7.63-7.27 (m, 5H); 7.03 (d, 2H, J=10Hz); 5.27 (s, 2H); 4.60 (bd, 2H, J=7Hz); 3.90 (q, 2H, J=7Hz); 3.34 (s, 2H); 2.47 (t, 2H J=7Hz); 1.48 (t of t, 2H, J=7,7Hz); 1.24 (t of q, 2H, J=7,7Hz); 1.06 (t, 3H, J=7Hz); 0.78 (t, 3H, J=7 Hz). Anal. Calcd. for C25H28ClN3O4.(H2O)0.33 : C, 63.17; H, 6.06; N, 8.83. Found: C, 63.30; H, 6.35; N, 8.44.

Sources & evidence

ORD record: ord-cc6ecd9303dc457db704046ae0de66a0
Source dataset: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05128355

Reaction notes

Loading…