Anisole → HCID 178503706, compound
Reaction equation
[NH:1]1[CH2:71][CH2:70][CH2:69][CH2:68][C@H:2]1[C:3]([NH:5][C@@H:6]([C:17]([NH:19][C@H:20]([C:28]([NH:30][C@@H:31]([C:49]([NH:51][C@H:52]([C:57]([NH:59][C@H:60]([C:65]([NH2:67])=[O:66])[CH2:61][CH2:62][S:63][CH3:64])=[O:58])[CH2:53][CH:54]([CH3:56])[CH3:55])=[O:50])[CH2:32][CH2:33][CH2:34][NH:35][C:36](=[NH:48])[NH:37]S(C1C=CC(C)=CC=1)(=O)=O)=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:18])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)=[O:4].F.C1(OC)C=CC=CC=1>>[NH:1]1[CH2:71][CH2:70][CH2:69][CH2:68][C@H:2]1[C:3]([NH:5][C@@H:6]([C:17]([NH:19][C@H:20]([C:28]([NH:30][C@@H:31]([C:49]([NH:51][C@H:52]([C:57]([NH:59][C@H:60]([C:65]([NH2:67])=[O:66])[CH2:61][CH2:62][S:63][CH3:64])=[O:58])[CH2:53][CH:54]([CH3:55])[CH3:56])=[O:50])[CH2:32][CH2:33][CH2:34][NH:35][C:36](=[NH:37])[NH2:48])=[O:29])[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:18])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)=[O:4]Participants
4
Procedure
Condensation of BocPro-DTrp-PheOH (Example 33, 658 mg.) and HDArg(Tos)-Leu-MetNH2 (630 mg.) using dicyclohexylcarbodiimide and 1-hydroxybenzotriazole gave BocPro-DTrp-Phe-DArg(Tos)-Leu-MetNH2 in 46% yield. De-t-butoxycarbonylation of BocPro-DTrp-Phe-DArg(Tos)-Leu-MetNH2 (524 mg.) using trifluoroacetic acid in dimethyl sulfide and ethanedithiol gave HPro-DTrp-Phe-DArg(Tos)-Leu-MetNH2 in 78% yield. De-p-toluenesulfonylation of HPro-DTrp-Phe-DArg(Tos)-Leu-MetNH2 (420 mg.) using liquid hydrogen fluoride with anisole gave HPro-DTrp-Phe-DArg-Leu-MetNH2, which was isolated as the amorphous off-white solid dihydrochloride acetate (2:1) salt hydrate (2:5) in 61% yield.
Sources & evidence
- ORD record
- ord-c6fe6d2870534728869699caf5f3febb
- Source dataset
- uspto-grants-1984_09
- Patent number
- US04472305
Reaction notes
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