(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 178460291, compound

HRID 1630167Notes

Reaction equation

HRID 1630167 reaction equation
Cl.[NH:2]1[CH:6]=[C:5]([CH:7]([CH3:11])[C:8]([OH:10])=O)[N:4]=[CH:3]1.[NH2:12][C@@H:13]([CH2:31][O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)=[O:15]>>[NH:2]1[CH:6]=[C:5]([CH:7]([CH3:11])[C:8]([NH:12][C@@H:13]([CH2:31][O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:14]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[CH:21][CH:22]=2)=[O:15])=[O:10])[N:4]=[CH:3]1

Participants

3

Reactant 2

HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideHCID 178460415HCID 178460415, compound

Product 1

HCID 178460291HCID 178460291, compoundYield 21%

Procedure

Proceeding as in Example 1, but substituting 2-(1H-imidazol-4-yl)propanoic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 167, (2S)-2-(2-(1H-imidazol-4-yl)propanamido)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide (49 mg, 21%). 1H-NMR (400 MHz, CDCl3): δ 9.80 (s, 1H), 9.46 (s, 1H), 9.38 (br s, 1H), 7.80-7.15 (m, 9H), 7.00-6.79 (m, 6H), 4.82-4.71 (m, 1H), 4.54-4.38 (m, 2H), 4.01-3.59 (m, 3H), 1.45-1.34 (m, 3H). MS (EI) for C28H27FN4O4 found 503 (MH+).

Sources & evidence

ORD record
ord-374226d3c2c145a69cc17bd72ed1c054
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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