(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 67009801, compound

HRID 1630142Notes

Reaction equation

HRID 1630142 reaction equation
Cl.[O:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]([OH:18])=O)[CH2:11][CH2:10]1)=[O:8].[NH2:19][C@@H:20]([CH2:38][O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)=[CH:26][CH:25]=1)=[O:22]>>[CH2:40]([O:39][CH2:38][C@H:20]([NH:19][C:16](=[O:18])[CH2:15][N:12]1[CH2:11][CH2:10][N:9]([C:7]([CH:3]2[CH2:4][CH2:5][CH2:6][O:2]2)=[O:8])[CH2:14][CH2:13]1)[C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)=[CH:26][CH:25]=1)=[O:22])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

3

Reactant 2

HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideHCID 67009287HCID 67009287, compound

Product 1

HCID 67009801HCID 67009801, compoundYield 39.9%

Procedure

Proceeding as in Example 1, but substituting 2-(4-(tetrahydrofuran-2-carbonyl)piperazin-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 237, (2S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(4-(tetrahydrofuran-2-carbonyl)piperazin-1-yl)acetamido)propanamide (19.3 mg, 39.9%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.24 (s, 1H), 8.03 (d, 1H), 7.61 (d, 2H), 7.30 (m, 5H), 7.21 (t, 2H), 7.04-6.99 (m, 4H), 4.70 (m, 1H), 4.65 (t, 1H), 4.53 (s, 2H), 3.78-3.72 (m, 4H), 3.35 (m, 6H), 3.04 (s, 2H), 2.44 (m, 2H), 1.97 (dd, 2H), 1.80 (m, 2H). MS (EI) for C33H37FN4O6. found 605.7 (MH+).

Sources & evidence

ORD record
ord-988da065b448470d8084ffed8b9abad3
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

Loading…