Trifluoroacetic acid → Trifluoroacetic acid

HRID 1271724Notes

Reaction equation

HRID 1271724 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[C@H:10]([NH:25][C:26](=[O:40])[C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]3=[O:39])=[CH:29][CH:28]=2)[CH2:9]1)=O)(C)(C)C.[F:41][C:42]([F:47])([F:46])[C:43]([OH:45])=[O:44]>C(Cl)Cl>[CH2:18]([O:17][C:15](=[O:16])[NH:14][C@H:11]1[CH2:12][CH2:13][NH:8][CH2:9][C@H:10]1[NH:25][C:26](=[O:40])[C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]2=[O:39])=[CH:29][CH:28]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:43]([OH:45])([C:42]([F:47])([F:46])[F:41])=[O:44]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69437112Cis-4-Benzyloxycarbonylamino-3-[4-(2-oxo-2H-pyridin-1-yl)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester

Product 2

HCID 6422Trifluoroacetic acidHCID 69146550HCID 69146550, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cis-4-Benzyloxycarbonylamino-3-[4-(2-oxo-2H-pyridin-1-yl)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester (22.2 mg, 0.041 mmol) was dissolved in 2 mL of anhydrous CH2Cl2 To this solution was added 2 mL of trifluoroacetic acid (TFA). The mixture was stirred for one hour at rt. The solvent was removed in vacuo to yield cis-{3-[4-(2-Oxo-2H-pyridin-1-yl)-benzoylamino]-piperidin-4-yl}-carbamic acid benzyl ester, CF3COOH salt (42.7 mg) as a viscous oil, which was used without any further purification. Anal. LC/MS (ESI) Shimadzu Phenomenex C18; 4.6×50 mm Luna; flow rate 4 mL/mn; detection at 220 nM; Gradient elution 0% to 100% B over 4 min; (A=10% MeOH, 90% H2O, 0.1% TFA & B=90% MeOH, 10% H2O, 0.1% TFA); 447.24 (M+H)+, tR=2.15 min.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-77b53efcb7814785a68640b997c2474f
Source dataset
uspto-grants-2007_04
Patent number
US07205318B2

Reaction notes

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