Trifluoroacetic acid → HCID 59655457, compound

HRID 2053590Notes

Reaction equation

HRID 2053590 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, 1H), 7.60-7.35 (m, 2H), 7.15-6.85 (m, 9H), 6.85-6.60 (m, 4H), 5.20 (s, 2H); 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-2ea79a8a688f4e098ee9c8c3dffbfb29
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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