HCID 67427351, compound → HCID 46833514, compound

HRID 1510292Notes

Reaction equation

HRID 1510292 reaction equation
C([O:5][C:6](=[O:43])[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:17][CH2:16][C@H:15]([O:18][C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26]([C:28]4[N:29]=[C:30]([C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=5)[O:31][C:32]=4[C:33]([F:36])([F:35])[F:34])=[O:27])=[CH:21][CH:20]=3)[CH2:14]2)=[CH:9][CH:8]=1)(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[C:37]1([C:30]2[O:31][C:32]([C:33]([F:36])([F:34])[F:35])=[C:28]([C:26]([NH:25][C:22]3[CH:21]=[CH:20][C:19]([O:18][C@H:15]4[CH2:16][CH2:17][N:13]([C:10]5[CH:11]=[CH:12][C:7]([C:6]([OH:43])=[O:5])=[CH:8][CH:9]=5)[CH2:14]4)=[CH:24][CH:23]=3)=[O:27])[N:29]=2)[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

4

Reactant 1

HCID 67427351HCID 67427351, compound

Product 1

HCID 46833514HCID 46833514, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The above 4-((S)-3-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenoxy}-pyrrolidin-1-yl)-benzoic acid tert-butyl ester (150 mg) was dissolved in a mixture of methylene chloride (2 mL) and trifluoroacetic acid (4 mL). The mixture was stirred at room temperature for 1 hr and solvents were evaporated. The residue was extracted with ethyl acetate and water. The organic layer was dried and solvents were evaporated. The residue was triturated with ethyl acetate and hexanes to give a tan solid as 4-((S)-3-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenoxy}-pyrrolidin-1-yl)-benzoic acid (75 mg). LC-MS for C28H22F3N3O5 (m/e) calcd 537, obsd 538 (M+H). 1H-NMR is consistent with the desired structure.

Workup

  1. customsolvents were evaporated
  2. extractionThe residue was extracted with ethyl acetate and water
  3. customThe organic layer was dried
  4. customsolvents were evaporated
  5. customThe residue was triturated with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-8d8c21450d854783b49c8f5d67f9dd6d
Source dataset
uspto-grants-2012_07
Patent number
US08211914B2

Reaction notes

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