Trifluoroacetic acid → HCID 178426694, compound

HRID 1823939Notes

Reaction equation

HRID 1823939 reaction equation
C(OC(=O)[NH:7][CH:8]([CH2:28][C:29]1[C:34]([CH3:35])=[CH:33][C:32]([C:36](=[O:38])[NH2:37])=[CH:31][C:30]=1[CH3:39])[C:9](=[O:27])[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[C:16]1[NH:17][CH:18]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:20]=1)(C)(C)C.FC(F)(F)C(O)=O>>[NH2:7][CH:8]([C:9](=[O:27])[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[C:16]1[NH:17][CH:18]=[C:19]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:20]=1)[CH2:28][C:29]1[C:30]([CH3:39])=[CH:31][C:32]([C:36]([NH2:37])=[O:38])=[CH:33][C:34]=1[CH3:35]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178426697HCID 178426697, compound

Product 1

HCID 178426694HCID 178426694, compound

Procedure

To {1-(4-carbamoyl-2,6-dimethyl-benzyl)-2-oxo-2-[2-(4-phenyl-1H-imidazol-2-yl)-piperidin-1-yl]-ethyl}-carbamic acid tert-butyl ester (0.60 g, 1.10 mmol) was added 0° C. trifluoroactic acid (4 mL). The resulting solution was warmed to room temperature, and after 30 minutes the excess trifluoroacetic acid was removed under a stream of nitrogen. This material was purified via a Gilson preparative HPLC resulting in the isolation of desired product 4-{2-amino-3-oxo-3-[2-(4-phenyl-1H-imidazol-2-yl)-piperidin-1-yl]-propyl}-3,5-dimethyl-benzamide as a white solid after lyophilization, which proved 100% pure by HPLC at 254 and 214 nm, (LC/MS; Measured MW (MH+): 446).

Workup

  1. customafter 30 minutes the excess trifluoroacetic acid was removed under a stream of nitrogen
  2. customThis material was purified via a Gilson preparative HPLC

Sources & evidence

ORD record
ord-9697d6b85f6c484fb665b4efa218e21e
Source dataset
uspto-grants-2006_05
Patent number
US07041681B2

Reaction notes

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