Trifluoroacetic acid → Fmoc-D-Lys-D-Lys-Leu-Leu-OH

HRID 537629Notes

Reaction equation

HRID 537629 reaction equation
[NH:1]([C:57]([O:59][CH2:60][CH:61]1[C:73]2[C:68](=[CH:69][CH:70]=[CH:71][CH:72]=2)[C:67]2[C:62]1=[CH:63][CH:64]=[CH:65][CH:66]=2)=[O:58])[C@@H:2]([C:15]([NH:17][C@@H:18]([C:31]([NH:33][C@H:34]([C:39]([NH:41][C@H:42]([C:47]([O:49]CC1C=CC=CC=1)=[O:48])[CH2:43][CH:44]([CH3:46])[CH3:45])=[O:40])[CH2:35][CH:36]([CH3:38])[CH3:37])=[O:32])[CH2:19][CH2:20][CH2:21][CH2:22][NH:23]C(OC(C)(C)C)=O)=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7]C(OC(C)(C)C)=O.FC(F)(F)C(O)=O.C([SiH](C(C)C)C(C)C)(C)C>O>[NH:1]([C:57]([O:59][CH2:60][CH:61]1[C:62]2[C:67](=[CH:66][CH:65]=[CH:64][CH:63]=2)[C:68]2[C:73]1=[CH:72][CH:71]=[CH:70][CH:69]=2)=[O:58])[C@@H:2]([C:15]([NH:17][C@@H:18]([C:31]([NH:33][C@H:34]([C:39]([NH:41][C@H:42]([C:47]([OH:49])=[O:48])[CH2:43][CH:44]([CH3:46])[CH3:45])=[O:40])[CH2:35][CH:36]([CH3:38])[CH3:37])=[O:32])[CH2:19][CH2:20][CH2:21][CH2:22][NH2:23])=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 138754Silane, tris(1-methylethyl)-HCID 131731956Fmoc-D-Lys(Boc)-D-Lys(Boc)-Leu-Leu-OBzl

Product 1

HCID 131731959Fmoc-D-Lys-D-Lys-Leu-Leu-OH

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The crude crystals (100 mg) of Fmoc-D-Lys(Boc)-D-Lys(Boc)-Leu-Leu-OBzl (2-MeO-4-OC12OC22) were added to a solution (2 ml) of trifluoroacetic acid:triisopropylsilane:water=95:2.5:2.5 under ice-cooling, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and methyl tert-butyl ether (MTBE)/cyclohexane was added to the residue. The precipitate was washed at 40° C. and collected by filtration to give Fmoc-D-Lys-D-Lys-Leu-Leu-OH (29 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and methyl tert-butyl ether (MTBE)/cyclohexane
  2. additionwas added to the residue
  3. washThe precipitate was washed at 40° C.
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-b29b86096c824b47b743b0ca8c253495
Source dataset
uspto-grants-2014_10
Patent number
US08859732B2

Reaction notes

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