Trifluoroacetic acid → N-[[2-(9H-Fluoren-9-yl)ethoxy]carbonyl]-L-leucine

HRID 1089834Notes

Reaction equation

HRID 1089834 reaction equation
C([O:5][C:6](=[O:31])[C@H:7]([CH2:27][CH:28]([CH3:30])[CH3:29])[NH:8][C:9]([O:11][CH2:12][CH2:13][CH:14]1[C:26]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:20]2[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:10])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:16]1[C:15]2[CH:14]([CH2:13][CH2:12][O:11][C:9]([NH:8][C@H:7]([C:6]([OH:31])=[O:5])[CH2:27][CH:28]([CH3:30])[CH3:29])=[O:10])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15045053HCID 15045053, compound

Product 1

HCID 15045054N-[[2-(9H-Fluoren-9-yl)ethoxy]carbonyl]-L-leucineYield 92.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6.63 g (15.6 mmol) of N-[(9H-fluoren-9-ylethoxy)carbonyl]-L-leucine tert-butyl ester in 10 mL of methylene chloride was added 10 mL of trifluoroacetic acid. The mixture was stirred for 2.5 h and solvent was removed at reduced pressure. The crude product was chromatographed on 150 g of flash silica gel eluting with 25% EtOAc in hexane followed by 50% EtOAc in hexane to afford 5.32 g (92%) of product as a white solid, mp 42°-43° C.

Workup

  1. customsolvent was removed at reduced pressure
  2. customThe crude product was chromatographed on 150 g of flash silica gel eluting with 25% EtOAc in hexane

Sources & evidence

ORD record
ord-bbf8a59e931a45da969b371c5f35333c
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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