Anisole → HCID 178462129, compound
Reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:19]([NH:21][C@H:22]([C:40]([N:42]1[CH2:81][CH2:80][CH2:79][C@H:43]1[C:44]([NH:46][C@H:47]([C:49]([NH:51][C@H:52]([C:69]([O:71]CC1C=CC=CC=1)=[O:70])[CH2:53][CH2:54][CH2:55][CH2:56][NH:57]C(OCC1C=CC=CC=1Cl)=O)=[O:50])[CH3:48])=[O:45])=[O:41])[CH2:23][CH2:24][CH2:25][NH:26][C:27](=[NH:39])[NH:28]S(C1C=CC(C)=CC=1)(=O)=O)=[O:20])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7]C(OCC1C=CC=CC=1Cl)=O.C1(OC)C=CC=CC=1>>[NH2:1][C@H:2]([C:19]([NH:21][C@H:22]([C:40]([N:42]1[CH2:81][CH2:80][CH2:79][C@H:43]1[C:44]([NH:46][C@H:47]([C:49]([NH:51][C@H:52]([C:69]([OH:71])=[O:70])[CH2:53][CH2:54][CH2:55][CH2:56][NH2:57])=[O:50])[CH3:48])=[O:45])=[O:41])[CH2:23][CH2:24][CH2:25][NH:26][C:27](=[NH:28])[NH2:39])=[O:20])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7]Participants
3
Conditions
- Temperature
- 0 °C
Procedure
The solution of 290 mg (0.227 mmol) of Boc-Lys(ClZ)-Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl (SEQ ID NO: 15), 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 130 mg (96%) of the title compound. Mp. 168–170° C., FAB-MS (m/e) 599[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-26b6cd4f008944bc964d66ba0f3615e0
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07138491B2
Reaction notes
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