(S)-2-amino-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → (S)-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(2-phenyloxazol-4-yl)acetamido)propanamide

HRID 1630151Notes

Reaction equation

HRID 1630151 reaction equation
Cl.[C:2]1([C:8]2[O:9][CH:10]=[C:11]([CH2:13][C:14]([OH:16])=O)[N:12]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][C@@H:18]([CH2:36][O:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=1)[C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)=[CH:24][CH:23]=1)=[O:20]>>[F:45][C:42]1[CH:43]=[CH:44][C:39]([CH2:38][O:37][CH2:36][C@H:18]([NH:17][C:14](=[O:16])[CH2:13][C:11]2[N:12]=[C:8]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[O:9][CH:10]=2)[C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)=[CH:24][CH:23]=2)=[O:20])=[CH:40][CH:41]=1

Participants

3

Reactant 2

HCID 67009398(S)-2-amino-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideHCID 670101232-(2-Phenyloxazol-4-yl)acetic acid hydrochloride

Product 1

HCID 45377297(S)-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(2-phenyloxazol-4-yl)acetamido)propanamideYield 70%

Procedure

Proceeding as in Example 1, but substituting 2-(2-phenyloxazol-4-yl)acetic acid hydrochloride and (S)-2-amino-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 44, (S)-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(2-phenyloxazol-4-yl)acetamido)propanamide (160 g, 70%). 1H-NMR (400 MHz, CDCl3): σ 8.45 (s, 1H), 8.00 (m, 2H), 7.50-7.45 (m, 2H), 7.40-7.30 (m, 7H), 7.05-6.80 (m, 8H), 4.79-4.73 (m, 1H), 4.63 (m, 2H), 4.00-3.70 (m, 4H). MS (EI) for C33H27F2N3O5 found 584 (MH+).

Sources & evidence

ORD record
ord-a76c053690d3427b9414e797e3721778
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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