Anisole → HCID 178462177, compound
Reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:4]([NH:6][C@H:7]([C:25]([N:27]1[CH2:66][CH2:65][CH2:64][C@H:28]1[C:29]([NH:31][C@H:32]([C:34]([NH:36][C@H:37]([C:54]([O:56]CC1C=CC=CC=1)=[O:55])[CH2:38][CH2:39][CH2:40][CH2:41][NH:42]C(OCC1C=CC=CC=1Cl)=O)=[O:35])[CH3:33])=[O:30])=[O:26])[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[NH:24])[NH:13]S(C1C=CC(C)=CC=1)(=O)=O)=[O:5])[CH3:3].C1(OC)C=CC=CC=1>>[NH2:1][C@H:2]([C:4]([NH:6][C@H:7]([C:25]([N:27]1[CH2:66][CH2:65][CH2:64][C@H:28]1[C:29]([NH:31][C@H:32]([C:34]([NH:36][C@H:37]([C:54]([OH:56])=[O:55])[CH2:38][CH2:39][CH2:40][CH2:41][NH2:42])=[O:35])[CH3:33])=[O:30])=[O:26])[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[NH:13])[NH2:24])=[O:5])[CH3:3]Participants
3
Conditions
- Temperature
- 0 °C
Procedure
The solution of 250 mg (0.237 mmol) of Boc-Ala-Arg(Tos)-Pro-Ala-Lys(ClZ)OBzl (SEQ ID NO: 13), 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 (77.8%) of the title compound. Mp. 224–6° C., FAB-MS (m/e) 542[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-2934ed8bf73d40f7b2629775314062e9
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07138491B2
Reaction notes
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