2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride → (S)-2-(2-(1H-1,2,4-triazol-1-yl)acetamido)-3-(benzyloxy)-N-(4-phenoxyphenyl)propanamide

HRID 1630092Notes

Reaction equation

HRID 1630092 reaction equation
Cl.[N:2]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[N:5][CH:4]=[N:3]1.[NH2:11][C@@H:12]([CH2:29][O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:18][CH:17]=1)=[O:14]>>[N:2]1([CH2:7][C:8]([NH:11][C@@H:12]([CH2:29][O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:13]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:20][CH:21]=2)=[O:14])=[O:10])[CH:6]=[N:5][CH:4]=[N:3]1

Participants

3

Reactant 2

HCID 448870502-(1H-1,2,4-triazol-1-yl)acetic acid hydrochlorideHCID 67009331(S)-2-amino-3-(benzyloxy)-N-(4-phenoxyphenyl)propanamide

Product 1

HCID 67009192(S)-2-(2-(1H-1,2,4-triazol-1-yl)acetamido)-3-(benzyloxy)-N-(4-phenoxyphenyl)propanamideYield 82%

Procedure

Proceeding as in Example 1, but substituting 2-(1,2,4)-triazol-1-ylacetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-phenoxyphenyl)propanamide, gave Compound 146, (S)-2-(2-(1H-1,2,4-triazol-1-yl)acetamido)-3-(benzyloxy)-N-(4-phenoxyphenyl)propanamide (106 mg, 82%). 1H-NMR (400 MHz, CDCl3): σ 8.69 (s, 1H), 8.41 (br s, 1H), 7.64 (d, 1H), 7.58 (d, 1H), 7.44 (d, 2H), 7.39-7.25 (m, 6H), 7.10-7.06 (m, 2H), 6.99-6.97 (m, 4), 5.03-4.99 (m, 1H), 4.76 (d, 1H), 4.65 (d, 1H), 4.25 (dd, 1H), 3.78 (dd, 1H). MS (EI) for C26H25N5O4. found 472.1 (MH+).

Sources & evidence

ORD record
ord-bc935d28f7c3470ebb428c55c963ea41
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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