Trifluoroacetic acid → HCID 21948338, compound

HRID 2214813Notes

Reaction equation

HRID 2214813 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(OC([N:15]1[CH2:20][CH2:19][C:18]([CH2:27][N:28]2[CH2:33][CH2:32][N:31]([C:34]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:35])[CH2:30][C:29]2=[O:44])([NH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:17][CH2:16]1)=O)(C)(C)C>C1(C)C=CC=CC=1>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:25]([O:24][C:22]([NH:21][C:18]1([CH2:27][N:28]2[CH2:33][CH2:32][N:31]([C:34]([O:36][CH2:37][C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)=[O:35])[CH2:30][C:29]2=[O:44])[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]1)=[O:23])[CH3:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21948278HCID 21948278, compound

Product 1

HCID 21948338HCID 21948338, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trifluoroacetic acid (78 ml) was added to a solution of benzyl 4-[[1-(tert-butoxycarbonyl)-4-[(ethoxycarbonyl)amino]-4-piperidinyl]methyl]-3-oxo-1-piperazinecarboxylate (26 g) obtained in Reference Example 7 in toluene (78 ml) at room temperature while stirring, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from ethyl acetate/diethyl ether=5/1) to obtain the title compound (16 g, 60%) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was crystallized from ethyl acetate/diethyl ether=5/1)

Sources & evidence

ORD record
ord-73e1174b5d094705ba6ba011ae884cf1
Source dataset
uspto-grants-2006_09
Patent number
US07109200B2

Reaction notes

Loading…