(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 67009775, compound

HRID 1630121Notes

Reaction equation

HRID 1630121 reaction equation
Cl.[CH2:2]1[CH:11]2[CH:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)[CH2:5][CH2:4][N:3]1[CH2:12][C:13]([OH:15])=O.[NH2:16][C@@H:17]([CH2:35][O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)=[O:19]>>[CH2:37]([O:36][CH2:35][C@H:17]([NH:16][C:13](=[O:15])[CH2:12][N:3]1[CH2:4][CH2:5][CH:6]2[CH:11]([CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:2]1)[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)=[O:19])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

3

Reactant 2

HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideHCID 67009403HCID 67009403, compound

Product 1

HCID 67009775HCID 67009775, compoundYield 46%

Procedure

Proceeding as in Example 1, but substituting 2-(octahydroisoquinolin-2(1H)-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 222, (2S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(octahydroisoquinolin-2(1H)-yl)acetamido)propanamide (20.6 mg, 46%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): 10.21 (s, 1H), 7.96 (d, 1H), 7.60 (d, 2H), 7.29-7.31 (m, 5H), 7.19-7.23 (m, 2H), 6.98-7.04 (m, 4H), 4.68 (m, 1H), 4.49 (s, 2H), 3.29-3.79 (m, 2H), 2.77-3.01 (m, 2H), 2.63-2.73 (m, 2H), 2.01-2.99 (m, 2H), 0.81-1.86 (m, 12H). MS (EI) for C33H38FN3O4. found 560.6 (MH+).

Sources & evidence

ORD record
ord-2c376a8af5454e3db7c74a2c5063304d
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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