3-(Dimethylamino)propanoic acid hydrochloride → (S)-3-(benzyloxy)-N-(4-(4-chlorophenoxy)phenyl)-2-(3-(dimethylamino)propanamido)propanamide

HRID 1630101Notes

Reaction equation

HRID 1630101 reaction equation
Cl.[CH3:2][N:3]([CH3:9])[CH2:4][CH2:5][C:6](O)=[O:7].[NH2:10][C@@H:11]([CH2:29][O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)=[O:13]>>[CH2:31]([O:30][CH2:29][C@H:11]([NH:10][C:6](=[O:7])[CH2:5][CH2:4][N:3]([CH3:9])[CH3:2])[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)=[O:13])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

3

Reactant 2

HCID 115863273-(Dimethylamino)propanoic acid hydrochlorideHCID 67009405(S)-2-amino-3-(benzyloxy)-N-(4-(4-chlorophenoxy)phenyl)propanamide

Product 1

HCID 67010449(S)-3-(benzyloxy)-N-(4-(4-chlorophenoxy)phenyl)-2-(3-(dimethylamino)propanamido)propanamideYield 10%

Procedure

Proceeding as in Example 1, but substituting 3-dimethylaminopropionic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-chlorophenoxy)phenyl)propanamide, gave Compound 209, (S)-3-(benzyloxy)-N-(4-(4-chlorophenoxy)phenyl)-2-(3-(dimethylamino)propanamido)propanamide (6 mg, 10%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.15 (br s, 1H), 8.48-8.47 (d, 1H), 7.65-7.61 (d, 2H), 7.42-7.39 (d, 2H), 7.43-7.39 (m, 2H), 7.32-7.26 (m, 5H), 7.06-6.96 (m, 4H), 4.72-4.67 (m, 1H), 4.52 (s, 2H), 3.65-3.64 (d, 2H), 2.47-2.43 (m, 2H), 2.33-2.30 (m, 2H), 2.12 (s, 6H). MS (EI) for C27H30ClN3O4. found 496.0 (MH+).

Sources & evidence

ORD record
ord-318dbdda8f954295a89d83233c75536f
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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