Trifluoroacetic acid → HCID 44129377, compound

HRID 2383330Notes

Reaction equation

HRID 2383330 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([C:19]2[O:23][N:22]=[C:21]([C:24]3[C:25]([CH3:47])=[C:26]4[C:31](=[CH:32][CH:33]=3)[CH:30]([CH2:34][CH2:35][CH2:36][C:37]([OH:39])=[O:38])[N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]4)[N:20]=2)[CH:12]=[N:13][C:14]=1[O:15][CH:16]([CH3:18])[CH3:17]>ClCCl>[Cl:8][C:9]1[CH:10]=[C:11]([C:19]2[O:23][N:22]=[C:21]([C:24]3[C:25]([CH3:47])=[C:26]4[C:31](=[CH:32][CH:33]=3)[CH:30]([CH2:34][CH2:35][CH2:36][C:37]([OH:39])=[O:38])[NH:29][CH2:28][CH2:27]4)[N:20]=2)[CH:12]=[N:13][C:14]=1[O:15][CH:16]([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59591076HCID 59591076, compound

Product 1

HCID 44129377HCID 44129377, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.0 ml) was added to a stirred solution of 4-(6-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-2-{[(1,1-dimethylethyl)oxy]carbonyl}-5-methyl-1,2,3,4-tetrahydro-1-isoquinolinyl)butanoic acid (Preparation 34; 50 mg, 0.09 mmol) in dry dichloromethane (3 ml). The reaction mixture was stirred at room temperature for 2 hours. The solvents were evaporated and the residue co-evaporated with toluene. Trituration of the residue with diethyl ether gave a gummy solid, which was purified by MDAP to give the title compound (26 mg) as a colourless solid.

Workup

  1. customThe solvents were evaporated
  2. customTrituration of the residue with diethyl ether gave a gummy solid, which
  3. customwas purified by MDAP

Sources & evidence

ORD record
ord-58a33491cefc454394fc49a38e722fe0
Source dataset
uspto-grants-2012_09
Patent number
US08263620B2

Reaction notes

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