Anisole → HCID 178462130, compound
Reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:20]([NH:22][C@H:23]([C:41]([N:43]1[CH2:82][CH2:81][CH2:80][C@H:44]1[C:45]([NH:47][C@H:48]([C:50]([NH:52][C@H:53]([C:70]([O:72]CC1C=CC=CC=1)=[O:71])[CH2:54][CH2:55][CH2:56][CH2:57][NH:58]C(OCC1C=CC=CC=1Cl)=O)=[O:51])[CH3:49])=[O:46])=[O:42])[CH2:24][CH2:25][CH2:26][NH:27][C:28](=[NH:40])[NH:29]S(C1C=CC(C)=CC=1)(=O)=O)=[O:21])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:19])[NH:8]S(C1C=CC(C)=CC=1)(=O)=O.C1(OC)C=CC=CC=1>>[NH2:1][C@H:2]([C:20]([NH:22][C@H:23]([C:41]([N:43]1[CH2:82][CH2:81][CH2:80][C@H:44]1[C:45]([NH:47][C@H:48]([C:50]([NH:52][C@H:53]([C:70]([OH:72])=[O:71])[CH2:54][CH2:55][CH2:56][CH2:57][NH2:58])=[O:51])[CH3:49])=[O:46])=[O:42])[CH2:24][CH2:25][CH2:26][NH:27][C:28](=[NH:29])[NH2:40])=[O:21])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:19]Participants
3
Conditions
- Temperature
- 0 °C
Procedure
The solution of 280 mg (0.188 mmol) of Boc-Arg(Tos)-Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl (SEQ ID NO: 18), 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 (85%) of the title compound. Mp. 168–170° C., FAB-MS (m/e) 627[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-fd76a0f3ab924ebfbfd916ee67d99722
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07138491B2
Reaction notes
Loading…