Trifluoroacetic acid → (r)-4-Amino-7-(2,2-dichloro-n-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-yl)acetamido)-5-oxoheptanoic acid trifluoroacetate salt

HRID 1782187Notes

Reaction equation

HRID 1782187 reaction equation
C(OC([NH:8][C@@H:9]([C:19](=[O:47])[CH2:20][CH2:21][N:22]([C:28]1[CH:33]=[CH:32][N:31]=[C:30]([C:34]2[O:38][N:37]=[C:36]([C:39]3[C:44]([Cl:45])=[CH:43][CH:42]=[CH:41][C:40]=3[Cl:46])[CH:35]=2)[CH:29]=1)[C:23](=[O:27])[CH:24]([Cl:26])[Cl:25])[CH2:10][CH2:11][C:12]([O:14]C(C)(C)C)=[O:13])=O)(C)(C)C.[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51]>ClCCl>[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51].[NH2:8][C@@H:9]([C:19](=[O:47])[CH2:20][CH2:21][N:22]([C:28]1[CH:33]=[CH:32][N:31]=[C:30]([C:34]2[O:38][N:37]=[C:36]([C:39]3[C:40]([Cl:46])=[CH:41][CH:42]=[CH:43][C:44]=3[Cl:45])[CH:35]=2)[CH:29]=1)[C:23](=[O:27])[CH:24]([Cl:26])[Cl:25])[CH2:10][CH2:11][C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57588466(R)-tert-butyl 4-(tert-butoxycarbonylamino)-7-(2,2-dichloro-N-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-yl)acetamido)-5-oxoheptanoate

Product 1

HCID 86608879(r)-4-Amino-7-(2,2-dichloro-n-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-yl)acetamido)-5-oxoheptanoic acid trifluoroacetate salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-tert-Butyl 4-(tert-butoxycarbonylamino)-7-(2,2-dichloro-N-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-yl)acetamido)-5-oxoheptanoate (165 mg) was dissolved in anhydrous dichloromethane (2 mL) and cooled in an ice-bath under nitrogen. Then trifluoroacetic acid (2 mL) was added. After 4.5 h at 4° C. the mixture was concentrated under reduced pressure. The residue was dissolved and concentrated under reduced pressure again to give (R)-4-amino-7-(2,2-dichloro-N-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-yl)acetamido)-5-oxoheptanoic acid trifluoroacetate salt as a tan solid. 1H NMR (CD3CN): 8.73 (m, 1H), 7.99 (m, 2H), 7.48 (m, 3H), 7.11 (s, 1H), 6.48 (s, 1H), 4.05 (m, 2H), 3.05-2.85 (m, 2H), 2.30 (m, 2H), 2.15 (m, 1H), 1.97 (m, 2H), 1.80 ppm (m, 1H). MW=594 confirmed by LC-MS, tr=10.07 min (Method Y) MH+=592-596.

Workup

  1. temperaturecooled in an ice-bath under nitrogen
  2. concentrationAfter 4.5 h at 4° C. the mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved
  4. concentrationconcentrated under reduced pressure again

Sources & evidence

ORD record
ord-8880890ba3a7468a93ddd53c721d32ae
Source dataset
uspto-grants-2009_03
Patent number
US07498353B2

Reaction notes

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