Trifluoroacetic acid → HCID 69670454, compound

HRID 1041925Notes

Reaction equation

HRID 1041925 reaction equation
FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+].[NH2:13][CH2:14][C:15]([O:17][CH2:18][C@H:19]([NH:21][C:22](=[O:53])[C:23]1[CH:28]=[CH:27][C:26]([C:29]2[N:33]=[C:32]([CH:34]([O:37][C:38]3[CH:43]=[CH:42][C:41]([C:44]4[N:48]=[C:47]([CH:49]5[CH2:51][CH2:50]5)[O:46][N:45]=4)=[CH:40][CH:39]=3)[CH2:35][CH3:36])[O:31][N:30]=2)=[CH:25][C:24]=1[F:52])[CH3:20])=[O:16].[ClH:54].C(OCC)(=O)C>C(OCC)(=O)C.C(Cl)Cl>[ClH:54].[NH2:13][CH2:14][C:15]([O:17][CH2:18][C@H:19]([NH:21][C:22](=[O:53])[C:23]1[CH:28]=[CH:27][C:26]([C:29]2[N:33]=[C:32]([CH:34]([O:37][C:38]3[CH:43]=[CH:42][C:41]([C:44]4[N:48]=[C:47]([CH:49]5[CH2:51][CH2:50]5)[O:46][N:45]=4)=[CH:40][CH:39]=3)[CH2:35][CH3:36])[O:31][N:30]=2)=[CH:25][C:24]=1[F:52])[CH3:20])=[O:16]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 69670455HCID 69670455, compound

Product 1

HCID 69670454HCID 69670454, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trifluoroacetic acid (1.00 mL) was added to a methylene chloride (1.00 mL) solution of the compound obtained in Reference Example 40 (260 mg, 0.391 mmol), and the mixture was stirred for one hour at room temperature. A saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and the mixture was subjected to extraction two times with ethyl acetate. The organic layer thus obtained was washed once with saturated brine, and then was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (ethyl acetate:methanol=9:1→4:1, v/v). To an ethyl acetate (500 μL) solution of the resulting (2R)-2-{[4-(5-{1-[4-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluorobenzoyl]amino}propyl glycinate (187 mg, 0.331 mmol), a 4 N hydrochloric acid-ethyl acetate solution (248 (L, 0.994 mmol) was added, and the solvent was distilled off under reduced pressure. Diethyl ether was added to the resulting residue, and the mixture was filtered. Thus, the title compound (170 mg, yield: 72%) was obtained.

Workup

  1. extractionthe mixture was subjected to extraction two times with ethyl acetate
  2. customThe organic layer thus obtained
  3. washwas washed once with saturated brine
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate:methanol=9:1→4:1, v/v)
  7. distillationthe solvent was distilled off under reduced pressure
  8. additionDiethyl ether was added to the resulting residue
  9. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-20b921808ba64af881cf6b2be1fe472a
Source dataset
uspto-grants-2013_10
Patent number
US08557802B2

Reaction notes

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