Anisole → H-Gln-Arg-Pro-Ala-Lys-OH
Reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:8]([NH:10][C@H:11]([C:29]([N:31]1[CH2:70][CH2:69][CH2:68][C@H:32]1[C:33]([NH:35][C@H:36]([C:38]([NH:40][C@H:41]([C:58]([O:60]CC1C=CC=CC=1)=[O:59])[CH2:42][CH2:43][CH2:44][CH2:45][NH:46]C(OCC1C=CC=CC=1Cl)=O)=[O:39])[CH3:37])=[O:34])=[O:30])[CH2:12][CH2:13][CH2:14][NH:15][C:16](=[NH:28])[NH:17]S(C1C=CC(C)=CC=1)(=O)=O)=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].C1(OC)C=CC=CC=1>>[NH2:1][C@H:2]([C:8]([NH:10][C@H:11]([C:29]([N:31]1[CH2:70][CH2:69][CH2:68][C@H:32]1[C:33]([NH:35][C@H:36]([C:38]([NH:40][C@H:41]([C:58]([OH:60])=[O:59])[CH2:42][CH2:43][CH2:44][CH2:45][NH2:46])=[O:39])[CH3:37])=[O:34])=[O:30])[CH2:12][CH2:13][CH2:14][NH:15][C:16](=[NH:17])[NH2:28])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6]Participants
3
Conditions
- Temperature
- 0 °C
Procedure
The solution of 250 mg (0.225 mmol) of Boc-Gln-Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl (SEQ ID NO: 16), 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 150 mg (98%) of the title compound. Mp. 180–182° C., FAB-MS (m/e) 600[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-6c145a7a75c84504b61c99cb190a7dff
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07138491B2
Reaction notes
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