(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 178521317, compound

HRID 1630125Notes

Reaction equation

HRID 1630125 reaction equation
Cl.[NH:2]1[CH:6]=[C:5]([CH2:7][CH2:8][NH:9][CH2:10][C:11]([OH:13])=O)[N:4]=[CH:3]1.[NH2:14][C@@H:15]([CH2:33][O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)=[O:17]>>[NH:2]1[CH:6]=[C:5]([CH2:7][CH2:8][NH:9][CH2:10][C:11]([NH:14][C@@H:15]([CH2:33][O:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:16]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[CH:23][CH:24]=2)=[O:17])=[O:13])[N:4]=[CH:3]1

Participants

3

Reactant 2

HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideHCID 178479766HCID 178479766, compound

Product 1

HCID 178521317HCID 178521317, compoundYield 26.3%

Procedure

Proceeding as in Example 1, but substituting 2-(2-(1H-imidazol-4-yl)ethylamino)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 216, (S)-2-(2-(2-(1H-imidazol-4-yl)ethylamino)acetamido)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide (11.2 mg, 26.3%). 1H-NMR (400 MHz, DMSO-D6): σ 10.24 (s, 1H), 8.25 (d, 1H), 7.61 (d, 2H), 7.51 (s, 1H), 7.28 (m, 6H), 7.19 (t, 2H), 7.02 (m, 4H), 6.78 (s, 1H), 4.70 (m, 1H), 4.52 (s, 2H), 3.68 (m, 3H), 3.20 (s, 2H), 2.75 (m, 2H), 2.64 (m, 2H). MS (EI) for C29H30FN5O4: 532.6 (MH+).

Sources & evidence

ORD record
ord-95b4b35672f844428e63bdffa774ab0b
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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