Anisole → HCID 178462133, compound
Reaction equation
[NH:1](C(OC(C)(C)C)=O)[CH2:2][C:3]([NH:5][C@H:6]([C:24]([N:26]1[CH2:65][CH2:64][CH2:63][C@H:27]1[C:28]([NH:30][C@H:31]([C:33]([NH:35][C@H:36]([C:53]([O:55]CC1C=CC=CC=1)=[O:54])[CH2:37][CH2:38][CH2:39][CH2:40][NH:41]C(OCC1C=CC=CC=1Cl)=O)=[O:34])[CH3:32])=[O:29])=[O:25])[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[NH:23])[NH:12]S(C1C=CC(C)=CC=1)(=O)=O)=[O:4].C1(OC)C=CC=CC=1>>[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:24]([N:26]1[CH2:65][CH2:64][CH2:63][C@H:27]1[C:28]([NH:30][C@H:31]([C:33]([NH:35][C@H:36]([C:53]([OH:55])=[O:54])[CH2:37][CH2:38][CH2:39][CH2:40][NH2:41])=[O:34])[CH3:32])=[O:29])=[O:25])[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[NH:12])[NH2:23])=[O:4]Participants
3
Conditions
- Temperature
- 0 °C
Procedure
The solution of 300 mg (0.289 mmol) of Boc-Gly-Arg(Tos)-Pro-Ala-Lys(ClZ)OBzl (SEQ ID NO: 14), 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 109 mg (80%) of the title compound. Mp. 168–170° C., FAB-MS (m/e) 528[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-9d6eb20f29794b8cba9a3d9426f6cee4
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07138491B2
Reaction notes
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