Trifluoroacetic acid → 2-Benzoyloxymethyl-5-[(6,2'-dimethyl-4'-propionylbiphenyl-3-ylamino)methyl]benzyl benzoate

HRID 584325Notes

Reaction equation

HRID 584325 reaction equation
[C:1]([O:9][CH2:10][C:11]1[CH:16]=[C:15]([CH2:17][N:18](C(OC(C)(C)C)=O)[C:19]2[CH:20]=[C:21]([C:26]3[CH:31]=[CH:30][C:29]([C:32](=[O:35])[CH2:33][CH3:34])=[CH:28][C:27]=3[CH3:36])[C:22]([CH3:25])=[CH:23][CH:24]=2)[CH:14]=[CH:13][C:12]=1[CH2:44][O:45][C:46](=[O:53])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[C:1]([O:9][CH2:10][C:11]1[CH:16]=[C:15]([CH2:17][NH:18][C:19]2[CH:20]=[C:21]([C:26]3[CH:31]=[CH:30][C:29]([C:32](=[O:35])[CH2:33][CH3:34])=[CH:28][C:27]=3[CH3:36])[C:22]([CH3:25])=[CH:23][CH:24]=2)[CH:14]=[CH:13][C:12]=1[CH2:44][O:45][C:46](=[O:53])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 697928892-Benzoyloxymethyl-5-{[tert-butoxycarbonyl(6,2'-dimethyl-4'-propionyl-biphenyl-3-yl)amino]methyl}benzyl benzoate

Product 1

HCID 697926032-Benzoyloxymethyl-5-[(6,2'-dimethyl-4'-propionylbiphenyl-3-ylamino)methyl]benzyl benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 g (1.4 mmol) of 2-benzoyloxymethyl-5-{[tert-butoxycarbonyl(6,2′-dimethyl-4′-propionyl-biphenyl-3-yl)amino]methyl}benzyl benzoate are dissolved in 50 ml of dichloromethane. 1,1 ml (14 mmol) of trifluoroacetic acid are added and the medium is stirred at room temperature for 6 hours. After extraction with water/dichloromethane, the desired product is obtained in the form of a yellowish oil (m=820 mg, Y=95%).

Workup

  1. extractionAfter extraction with water/dichloromethane

Sources & evidence

ORD record
ord-640904a968d24a97a6d173a3a71282b8
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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