Potassium Bromide → HCID 178520707, compound

HRID 1182519Notes

Reaction equation

HRID 1182519 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][C:12]2[N:13]=[C:14]([C:17]([N:19]3[CH2:33][CH2:32][CH2:31][C@H:20]3[C:21]([NH:23][CH:24]([CH:29]=[O:30])[CH2:25][C:26]([OH:28])=[O:27])=[O:22])=[O:18])[NH:15][CH:16]=2)=[CH:5][CH:4]=1.[K+].[Br-]>CO>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][C:12]2[N:13]=[C:14]([C:17]([N:19]3[CH2:33][CH2:32][CH2:31][C@H:20]3[C:21]([NH:23][CH:24]([CH:29]=[O:30])[CH2:25][C:26]([OH:28])=[O:27])=[O:22])=[O:18])[NH:15][CH:16]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 253877Potassium BromideHCID 178490053HCID 178490053, compound

Product 1

HCID 178520707HCID 178520707, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-{N-[4-[3-(4-Methoxyphenyl)propyl]imidazole-2-carbonyl]-L-prolinyl}amino-4-oxobutanoic acid (21e), was isolated (65%) as a white glassy solid: mp. 101-105° C.; [α]D23 −60.6 (c 0.05, MeOH); IR (KBr) 3231, 1784, 1726, 1611, 1512, 1245; 1H NMR(CD3OD) δ 7.09 (2H, d, J=8.6), 6.92, 6.85 (1H, 2×s), 6.81 (2H, d, J=8.6), 5.45-5.30 (1H, m), 4.64-4.46 (1H, m), 4.28-4.10 (2H, m), 3.75 (3H, s), 3.74-3.66 (1H, m), 2.67-1.84 (13H, m). Anal. Calcd for C23H28N4O6 H2O: C, 58.22; H, 6.37; N, 11.81. Found: C, 58.39; H, 6.34; N, 11.45; FABMS m/e 457 (M+), 405, 312, 243, 215, 176, 154 (100%) (3S) 3-{N-[4-[3-(4-Hydroxyphenyl)propyl]imidazole-2-carbonyl]-L-prolinyl}amino-4-oxobutanoic acid (21f), was isolated (43%) as a white glassy solid: mp. 114-118° C.; [α]D25-55.7° (c 0.05, MeOH); IR (KBr) 3288, 2935, 1780, 1715, 1662, 1610, 1515, 1441; 1H NMR(CD3OD) δ 6.99 (2H, d, J=8.5), 6.91, 6.85 (1H, 2×s), 6.68 (2H, d, J=8.5), 5.45-5.30 (1H, m), 4.60-4.47 (1H, m), 4.30-4.10 (2H, m), 3.80-3.55 (1H, m), 2.70-1.80 (13H, m). Anal. Calcd for C22H26N4O6 H2O: C, 57.38; H, 6.13; N, 12.17. Found: C, 57.68; H, 6.25; N, 11.66. FABMS m/e 443 (M+), 298, 229, 154 (100%). 3(S)-[(1-{5-[3-(4-Methoxyphenyl)propyl]-1H-imidazole-2-carbonyl}-4(R)-phenoxy pyrrolidine-2(S)-carbonyl)amino]-4-oxobutanoic acid (22e) was isolated (43%) as a beige solid: 1H NMR (CD3OD) δ 7.35-7.2 (3H, m), 7.15-7.0 (2H, m), 6.98-6.85 (3H, m), 6.83-6.77 (2H, d), 5.4-5.1 (1H, m), 4.65-4.5 (1H, m), 4.35-4.2 (2H, m), 4.15-3.90 (1H, m), 3.78 (3H, s), 3.62-3.48 (1H, m), 2.78-2.25 (8H, m), 2.02-1.9 (2H, m).

Sources & evidence

ORD record
ord-639f7e88e3e746678d34ceb2c0a2fc60
Source dataset
uspto-grants-2007_10
Patent number
US07288624B2

Reaction notes

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