(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 67010230, compound
Reaction equation
Cl.[C:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]([OH:20])=O)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)(=[O:4])[CH3:3].[NH2:21][C@@H:22]([CH2:40][O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)=[CH:28][CH:27]=1)=[O:24]>>[C:2]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:12][CH2:13][N:14]([CH2:17][C:18]([NH:21][C@@H:22]([CH2:40][O:41][CH2:42][C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[C:23]([NH:25][C:26]3[CH:27]=[CH:28][C:29]([O:32][C:33]4[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=4)=[CH:30][CH:31]=3)=[O:24])=[O:20])[CH2:15][CH2:16]2)=[CH:9][CH:10]=1)(=[O:4])[CH3:3]Participants
3
Procedure
Proceeding as in Example 1, but substituting 2-(4-(4-acetylphenyl)piperazin-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 229, (S)-2-(2-(4-(4-acetylphenyl)piperazin-1-yl)acetamido)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide (10.2 mg, 20.4%). 1H-NMR (400 MHz, DMSO-D6): σ 10.23 (s, 1H), 8.04 (d, 1H), 7.81 (d, 2H), 7.60 (d, 2H), 7.23 (m, 7H), 7.01 (m, 6H), 4.71 (m, 1H), 4.52 (s, 2H), 3.74 (m, 1H), 3.33 (m, 5H), 3.07 (s, 2H), 2.61 (m, 4H), 2.46 (s, 3H). MS (EI) for C36H37FN4O5: 625.6 (MH+).
Sources & evidence
- ORD record
- ord-0a44764c203b49f89342b0290fe87b23
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08791102B2
Reaction notes
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