Potassium Bromide → HCID 178462110, compound

HRID 1182518Notes

Reaction equation

[CH2:1]([C:8]1[N:9]=[C:10]([C:13]([NH:15][C@@H:16]([C:18]([NH:20][C@H:21]2[CH2:25][C:24](=[O:26])[O:23][C@@H:22]2[O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:19])[CH3:17])=[O:14])[NH:11][CH:12]=1)C1C=CC=CC=1.[K+].[Br-]>>[C:29]1([CH2:28][CH2:1][C:8]2[N:9]=[C:10]([C:13]([NH:15][C@@H:16]([C:18]([NH:20][C@H:21]3[CH2:25][C:24](=[O:26])[O:23][C@@H:22]3[O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:19])[CH3:17])=[O:14])[NH:11][CH:12]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Reactant 2

HCID 253877Potassium Bromide

HCID 178462109HCID 178462109, compound

Product 1

HCID 178462110HCID 178462110, compound

Procedure

(2R,S,3S) N2-(4-Benzylimidazole-2-carbonyl)-N-(tetrahydro-2-benzyloxy-5-oxo-3-furanyl)-L-alaninamide (17b), was isolated (75%) as a pale yellow glass: IR (KBr) 3294, 3031, 2937, 1792, 1650, 1530, 1453, 1444, 1119; 1H NMR(CDCl3) δ 7.99 (brm), 7.75 (brd), 7.36-7.11 (10H, m), 6.81 (1H, s), 5.51, 5.45 (d, s, J=5.3), 4.85-4.47 (4H, m), 3.95 (2H, s), 3.04-2.72 (1H, m), 2.48-2.35 (1H, m), 1.44 (d, J=6.9), 1.43 (d, J=7.1). (2R,S,3S) N2-[4-(2-Phenylethyl)imidazole-2-carbonyl]-N-(tetrahydro-2-benzyloxy-5-oxo-3-furanyl)-L-alaninamide (17c), was isolated (79%) as a pale yellow glass: IR (KBr) 3292, 3029, 2936, 1793, 1650, 1530, 1453, 1444, 1119; 1H NMR(CDCl3) δ 8.06 (brm), 7.70 (brs), 7.39-7.15 (10H, m), 6.82 (s), 6.81 (s), 5.53 (d, J=5.2), 5.48 (s), 4.87-4.53 (4H, m), 2.95 (4H, m), 3.11-2.37 (2H, m), 1.48 (d, J=5.6), 1.45 (d, J=6.7). (2R,S,3S) 1-[4-(2-Phenylethyl)imidazole-2-carbonyl]-N-(tetrahydro-2-benzyloxy-5-oxo-3-furanyl)-L-prolinamide (18c), was isolated (79%) as a pale yellow glass: IR (CH2Cl2) 3422, 2959, 1795, 1685, 1611, 1497, 1116;

Sources & evidence

ORD record: ord-807ab4e6f1f54e8aab4e6c51b54b4512
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07288624B2

Reaction notes

Loading…