Benzenamine, 4-(4-fluorophenoxy)- → (S)-2-amino-N-(4-(4-fluorophenoxy)phenyl)-3-(2-(trifluoromethoxy)benzyloxy)propanamide

HRID 1630064Notes

Reaction equation

HRID 1630064 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C(OC([NH:23][C@@H:24]([CH2:28][O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[O:37][C:38]([F:41])([F:40])[F:39])[C:25](O)=[O:26])=O)(C)(C)C>>[NH2:23][C@@H:24]([CH2:28][O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[O:37][C:38]([F:39])([F:40])[F:41])[C:25]([NH:11][C:10]1[CH:12]=[CH:13][C:7]([O:6][C:5]2[CH:14]=[CH:15][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:8][CH:9]=1)=[O:26]

Participants

3

Reactant 2

HCID 147633Benzenamine, 4-(4-fluorophenoxy)-HCID 67009145(S)-2-(tert-butoxycarbonylamino)-3-(2-(trifluoromethoxy)benzyloxy)propanoic acid

Product 1

HCID 67010385(S)-2-amino-N-(4-(4-fluorophenoxy)phenyl)-3-(2-(trifluoromethoxy)benzyloxy)propanamideYield 80%

Procedure

Proceeding as in Reference 5, but substituting 4-(4-fluorophenoxy)aniline and (S)-2-(tert-butoxycarbonylamino)-3-(2-(trifluoromethoxy)benzyloxy)propanoic acid, gave (S)-2-amino-N-(4-(4-fluorophenoxy)phenyl)-3-(2-(trifluoromethoxy)benzyloxy)propanamide (150 mg, 80%).

Sources & evidence

ORD record
ord-8fa5179c54a5475bb4380b3dccdb34ec
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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