3-Bromo-5-methoxybenzoic acid → N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-bromo-5-methoxybenzamide

HRID 1612440Notes

Reaction equation

HRID 1612440 reaction equation
[CH2:1]([C@H:8]([NH:23][C:24](=[O:33])[C:25]1[CH:30]=[CH:29][C:28](F)=[C:27]([Br:32])[CH:26]=1)[C@@H:9]([OH:22])[CH2:10][C@H:11]([C:13](=[O:21])[NH:14][CH2:15][CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C12CC(CC1)CC2NC(=O)[C@H](C)C[C@H:45]([OH:55])[C@@H](N)CC1C=CC=CC=1.BrC1C=C(C=C(OC)C=1)C(O)=O>>[CH2:1]([C@H:8]([NH:23][C:24](=[O:33])[C:25]1[CH:30]=[C:29]([O:55][CH3:45])[CH:28]=[C:27]([Br:32])[CH:26]=1)[C@@H:9]([OH:22])[CH2:10][C@H:11]([C:13](=[O:21])[NH:14][CH2:15][CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 40600483-Bromo-5-methoxybenzoic acidHCID 68889549(2R,4S,5S)-5-Amino-4-hydroxy-2-methyl-6-phenylhexanoic acid (bicyclo[2.2.1]hept-2-yl)amideHCID 69589710N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-bromo-4-fluorobenzamide

Product 1

HCID 69589673N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-bromo-5-methoxybenzamide

Procedure

Prepared as for D3 from (2R,4S,5S)-5-amino-4-hydroxy-2-methyl-6-phenylhexanoic acid (bicyclo[2.2.1]hept-2-yl)amide (D29) and 3-bromo-5-methoxybenzoic acid.

Sources & evidence

ORD record
ord-db069cfd24924ed1974cfe58c55d1a70
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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