Trifluoroacetic acid → HCID 59655349, compound

HRID 2053589Notes

Reaction equation

HRID 2053589 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:34])[CH2:9][C:10]2[N:11](C(OC(C)(C)C)=O)[C@H:12]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@H:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>ClCCl>[C:21]1([C@H:12]2[C@@H:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:14][C:10]([CH2:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[O:34])=[N:11]2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 865963372-[2-(4-Fluorophenyl)-2-oxoethyl]-cis-4,5-diphenyl-4,5-dihydro-imidazole-1-carboxylic Acid, Tert-Butyl Ester

Product 1

HCID 59655349HCID 59655349, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of 257 (458 mg, 1.0 mmol) in dichloromethane (25 mL) is added TFA (1.5 mL). The reaction mixture is stirred for 20 min. at 0° C., and at RT for 30 min. The solution is poured into cold sat. sodium bicarbonate solution, and the mixture extracted with EtOAc. The organic layer is separated, dried (MgSO4), and filtered. The filtrate is rotary evaporated, and the residue is recrystallized from Et2O to give 170 mg of the product 258. 1H NMR (CDCl3) δ 10.60-8.80 (bs, 1H), 8.00-7.80 (m, 2H), 7.20-7.00 (m, 9H), 7.00-6.85 (m, 4H), 5.50 (bs, 1H), 5.30 (s, 2H); MS: m/z 359 (M++1).

Workup

  1. waitat RT for 30 min
  2. extractionthe mixture extracted with EtOAc
  3. customThe organic layer is separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe residue is recrystallized from Et2O

Sources & evidence

ORD record
ord-c4f0367189994cd6a98bbba40f973abe
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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