Trifluoroacetic acid → HCID 58136477, compound

HRID 877261Notes

Reaction equation

HRID 877261 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][CH2:10][CH:11]([CH3:52])[CH:12]([C:32]1[CH:37]=[CH:36][C:35]([CH2:38][N:39]2[C:44](=[O:45])[CH2:43][O:42][C:41]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)=[N:40]2)=[CH:34][CH:33]=1)[C:13]([NH:15][C:16]1[C:17]([CH3:31])=[C:18]([CH2:22][CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])[CH:19]=[CH:20][CH:21]=1)=[O:14]>ClCCl>[CH3:8][O:9][CH2:10][CH:11]([CH3:52])[CH:12]([C:32]1[CH:37]=[CH:36][C:35]([CH2:38][N:39]2[C:44](=[O:45])[CH2:43][O:42][C:41]([C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)=[N:40]2)=[CH:34][CH:33]=1)[C:13]([NH:15][C:16]1[C:17]([CH3:31])=[C:18]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])[CH:19]=[CH:20][CH:21]=1)=[O:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58136348HCID 58136348, compound

Product 1

HCID 58136477HCID 58136477, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.27 ml (3.45 mmol) of trifluoroacetic acid was added dropwise to a solution of 106 mg (0.17 mmol) of tert-butyl 3-{3-[(4-methoxy-3-methyl-2-{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}butanoyl)amino]-2-methylphenyl}propanoate (Example 170A) in 2 ml of dichloromethane, and the mixture was stirred at room temperature for 3 h. The reaction solution was then concentrated to dryness under reduced pressure. The residue obtained was purified by preparative HPLC. This gave 66 mg (0.12 mmol, 68% of theory) of the title compound as a mixture of diastereomers.

Workup

  1. concentrationThe reaction solution was then concentrated to dryness under reduced pressure
  2. customThe residue obtained
  3. customwas purified by preparative HPLC
  4. additionThis gave 66 mg (0.12 mmol, 68% of theory) of the title compound as a mixture of diastereomers

Sources & evidence

ORD record
ord-ccde9ae41d1f444cbea951f3dba2759e
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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