(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 67009727, compound

HRID 1630130Notes

Reaction equation

HRID 1630130 reaction equation
Cl.[N:2]1([CH2:12][C:13]([OH:15])=O)[CH:11]2[CH:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)[CH2:5][CH2:4][CH2:3]1.[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:2]1[CH:11]2[CH:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)[CH2:5][CH2:4][CH2:3]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 67010209HCID 67010209, compound

Product 1

HCID 67009727HCID 67009727, compoundYield 44.9%

Procedure

Proceeding as in Example 1, but substituting 2-(octahydroquinolin-1(2H)-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 45, (2S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(octahydroquinolin-1(2H)-yl)acetamido)propanamide (20.1 mg, 44.9%). 1H-NMR (400 MHz, DMSO-D6): σ 10.22 (s, 1H), 7.84 (m, 1H), 7.59 (d, 2H), 7.28 (m, 7H), 7.02 (m, 4H), 4.69 (m, 1H), 4.51 (m, 2H), 3.73 (m, 2H), 3.34 (m, 2H), 3.33 (m, 2H), 2.97 (m, 1H), 2.75 (m, 1H), 2.17 (m, 1H), 1.42 (m, 11H). MS (EI) for C33H38FN3O4: 560.5 (MH+).

Sources & evidence

ORD record
ord-fbe37ab7384d4907aefd19248f81408a
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

Loading…