Acetate-hydrochloric acid → (S)-2-acetamido-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide

HRID 1630152Notes

Reaction equation

HRID 1630152 reaction equation
Cl.[C:2](O)(=[O:4])[CH3:3].[NH2:6][C@@H:7]([CH2:25][O:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)=[O:9]>>[C:2]([NH:6][C@@H:7]([CH2:25][O:26][CH2:27][C:28]1[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=1)[C:8]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[CH:15][CH:16]=1)=[O:9])(=[O:4])[CH3:3]

Participants

3

Reactant 2

HCID 22641269Acetate-hydrochloric acidHCID 67009398(S)-2-amino-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide

Product 1

HCID 45378168(S)-2-acetamido-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideYield 60%

Procedure

Proceeding as in Example 1, but substituting acetic acid hydrochloride and (S)-2-amino-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 164, (S)-2-acetamido-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide (35 mg, 60%). 1H-NMR (400 MHz, CDCl3): δ 8.40 (s, 1H), 7.40-7.25 (m, 5H), 7.10-6.90 (m, 7H), 6.45-6.40 (m, 1H), 4.80-4.45 (m, 3H), 4.00-3.90 (m, 1H), 3.60 (m, 1H), 1.60 (s, 3H). MS (EI) for C24H22F2N2O4 found 441 (MH+).

Sources & evidence

ORD record
ord-43d67f6231ca43959d43e8903c2dbaf6
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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