(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 67010600, compound

HRID 1630138Notes

Reaction equation

HRID 1630138 reaction equation
Cl.[CH3:2][N:3]1[CH2:7][CH2:6][CH2:5][C@H:4]1[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]1[CH2:15][C:16]([OH:18])=O.[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:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH:9]1[CH2:8][C@@H:4]1[CH2:5][CH2:6][CH2:7][N:3]1[CH3:2])[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 67009240HCID 67009240, compound

Product 1

HCID 67010600HCID 67010600, compoundYield 43.3%

Procedure

Proceeding as in Example 1, but substituting 2-(2-(((S)-1-methylpyrrolidin-2-yl)methyl)piperidin-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 113, (2S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(2-(((S)-1-methylpyrrolidin-2-yl)methyl)piperidin-1-yl)acetamido)propanamide (20.9 mg, 43.3%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.27 (d, 1H), 8.51 (s, 1H), 7.67-7.64 (m, 2H), 7.31 (m, 5H), 7.21 (t, 2H), 7.03-6.98 (m, 4H), 4.72 (m, 1H), 4.52 (d, 2H), 4.16 (m, 1H), 4.04 (m, 1H), 3.77-3.73 (m, 4H), 3.38 (s, 2H), 2.99 (s, 2H), 2.79 (m, 1H), 2.43 (m, 2H), 2.32 (m, 2H), 2.18 (m, 1H), 1.99 (m, 2H), 1.75 (m, 1H), 1.51 (m, 4H), 1.37 (m, 2H). MS (EI) for C35H43FN4O4. found 603.7 (MH+).

Sources & evidence

ORD record
ord-be8c6027190549919cb31ea597841522
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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