(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 67009185, compound

HRID 1630111Notes

Reaction equation

HRID 1630111 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]([OH:19])=O)[CH2:12][CH2:11]1.[NH2:20][C@@H:21]([CH2:39][O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:22]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)=[CH:27][CH:26]=1)=[O:23]>>[CH2:41]([O:40][CH2:39][C@H:21]([NH:20][C:17](=[O:19])[CH2:16][N:13]1[CH2:12][CH2:11][N:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[O:3][CH3:2])[CH2:15][CH2:14]1)[C:22]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)=[CH:27][CH:26]=1)=[O:23])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

3

Reactant 2

HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideHCID 67010631HCID 67010631, compound

Product 1

HCID 67009185HCID 67009185, compoundYield 38.8%

Procedure

Proceeding as in Example 1, but substituting 2-(4-(2-methoxyphenyl)piperazin-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 217, (S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(4-(2-methoxyphenyl)piperazin-1-yl)acetamido)propanamide (19 mg, 38.8%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.23 (1H), 5.02 (d, 1H), 7.61 (d, 2H), 7.25-4.30 (m, 4H), 7.20-7.23 (m, 3H), 4.00-7.04 (m, 3H), 6.85-6.98 (m, 5H), 4.71 (m, 1H), 4.53 (s. 2H), 3.80 (m, 1H), 3.77 (s, 3H), 3.72 (m, 1H), 3.05 (d, 2H), 2.99 (m, 4H), 2.62 (m, 4H). MS (EI) for C35H37FN4O5. found 613.6 (MH+).

Sources & evidence

ORD record
ord-6d8b0cc856ce4a7e8aeca1397477f4ab
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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