Trifluoroacetic acid → HCID 59655457, compound

HRID 18797Notes

Reaction equation

HRID 18797 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[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>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]2[NH:14][C@H:13]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C@H:12]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:11]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86596336HCID 86596336, compound

Product 1

HCID 59655457HCID 59655457, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) solution of 2-[2-(4-fluorophenyl)-2-hydroxyethyl]-cis-4,5-diphenyl-4,5-dihydro-imidazole-1-carboxylic acid, tert-butyl ester (256) (690 mg, 1.5 mmol) in dichloromethane (2 mL) is added TFA (2 mL). The reaction mixture is stirred at RT overnight. Reaction mixture is rotary evaporated and the residue purified by chromatography on silica gel; elution with dichloromethane:MeOH (9:1) gives 110 mg of the product 259. 1H NMR (CDCl3) δ 8.10 (d, 1 H), 7.60-7.35 (m, 2 H), 7.15-6.85 (m, 9 H), 6.85-6.60 (m, 4 H), 5.20 (s, 2 H); MS: m/z 343 (M++1).

Workup

  1. customReaction mixture
  2. customis rotary evaporated
  3. customthe residue purified by chromatography on silica gel
  4. washelution with dichloromethane:MeOH (9:1)

Sources & evidence

ORD record
ord-d8a93b6a182c4ce99c179a0b0ca6ddbb
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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