Anisole → L-Lysine, L-prolyl-L-alanyl-
Reaction equation
[N:1]1(C(OC(C)(C)C)=O)[CH2:40][CH2:39][CH2:38][C@H:2]1[C:3]([NH:5][C@H:6]([C:8]([NH:10][C@H:11]([C:28]([O:30]CC1C=CC=CC=1)=[O:29])[CH2:12][CH2:13][CH2:14][CH2:15][NH:16]C(OCC1C=CC=CC=1Cl)=O)=[O:9])[CH3:7])=[O:4].C1(OC)C=CC=CC=1>>[NH:1]1[CH2:40][CH2:39][CH2:38][C@H:2]1[C:3]([NH:5][C@H:6]([C:8]([NH:10][C@H:11]([C:28]([OH:30])=[O:29])[CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])=[O:9])[CH3:7])=[O:4]Participants
3
Conditions
- Temperature
- 0 °C
Procedure
The solution of 280 mg (0.417 mmol) of Boc-Pro-Ala-Lys(ClZ)-OBzl, 1 ml of anisole and 2 ml of HF was stirred at 0° C. for 2 h. The reaction mixture was evaporated under reduced pressure to remove HF. To the residue 2 ml of HF were added and the solution was stirred at 0° C. for another 1 h. The reaction mixture was evaporated under reduced pressure to remove HF. The residue was triturated with ether and the resulted solid was purified on the Sephadex G-10 column. The collected fractions were lyophilized to provide 100 mg (75%) of the title compound. Mp. 150–152° C., FAB-MS (m/e) 315[M+H]+.
Workup
- customThe reaction mixture was evaporated under reduced pressure
- customto remove HF
- additionTo the residue 2 ml of HF were added
- customThe reaction mixture was evaporated under reduced pressure
- customto remove HF
- customThe residue was triturated with ether
- customthe resulted solid was purified on the Sephadex G-10 column
Sources & evidence
- ORD record
- ord-eec0970bfd8d45fa9f3404d45b5b1ddf
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07138491B2
Reaction notes
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