Anisole → HCID 178462132, compound
Reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:7]([NH:9][C@H:10]([C:28]([N:30]1[CH2:69][CH2:68][CH2:67][C@H:31]1[C:32]([NH:34][C@H:35]([C:37]([NH:39][C@H:40]([C:57]([O:59]CC1C=CC=CC=1)=[O:58])[CH2:41][CH2:42][CH2:43][CH2:44][NH:45]C(OCC1C=CC=CC=1Cl)=O)=[O:38])[CH3:36])=[O:33])=[O:29])[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[NH:27])[NH:16]S(C1C=CC(C)=CC=1)(=O)=O)=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].C1(OC)C=CC=CC=1>>[NH2:1][C@H:2]([C:7]([NH:9][C@H:10]([C:28]([N:30]1[CH2:69][CH2:68][CH2:67][C@H:31]1[C:32]([NH:34][C@H:35]([C:37]([NH:39][C@H:40]([C:57]([OH:59])=[O:58])[CH2:41][CH2:42][CH2:43][CH2:44][NH2:45])=[O:38])[CH3:36])=[O:33])=[O:29])[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[NH:16])[NH2:27])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5]Participants
3
Conditions
- Temperature
- 0 °C
Procedure
The solution of 102 mg (0.1 mmol) of Boc-Asn-Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl (SEQ ID NO: 17), 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 43 mg (80%) of the title compound. Mp. 168–170° C., FAB-MS (m/e) 585[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-c2bc62f2b6454fcbb4d3fddd17ed1f39
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07138491B2
Reaction notes
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