Dicyclohexylcarbodiimide → BocPro-DTrp-Gly-DTrp-Leu-MetNH2

HRID 2418614Notes

Reaction equation

HRID 2418614 reaction equation
[N:1]1([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][CH2:25][CH2:24][C@H:2]1[C:3]([NH:5][C@@H:6]([C:17]([NH:19][CH2:20][C:21](O)=[O:22])=[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].[NH2:34][C@@H:35]([C:46]([NH:48][C@H:49]([C:54]([NH:56][C@H:57]([C:62]([NH2:64])=[O:63])[CH2:58][CH2:59][S:60][CH3:61])=[O:55])[CH2:50][CH:51]([CH3:53])[CH3:52])=[O:47])[CH2:36][C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[NH:39][CH:38]=1.FC(C(O)=O)(F)F.C1(N=C=NC2CCCCC2)CCCCC1.ON1C(=O)CCC1=O>>[N:1]1([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][CH2:25][CH2:24][C@H:2]1[C:3]([NH:5][C@@H:6]([C:17]([NH:19][CH2:20][C:21]([NH:34][C@@H:35]([C:46]([NH:48][C@H:49]([C:54]([NH:56][C@H:57]([C:62]([NH2:64])=[O:63])[CH2:58][CH2:59][S:60][CH3:61])=[O:55])[CH2:50][CH:51]([CH3:53])[CH3:52])=[O:47])[CH2:36][C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[NH:39][CH:38]=1)=[O:22])=[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

5

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 131713755HDTrp-Leu-MetNH2 trifluoroacetateHCID 131713804BocPro-DTrp-GlyOH

Product 1

HCID 131713803BocPro-DTrp-Gly-DTrp-Leu-MetNH2Yield 36%

Procedure

Condensation of BocPro-DTrp-GlyOH (1.00 g.) and HDTrp-Leu-MetNH2 trifluoroacetate salt (1.10 g.) using dicyclohexylcarbodiimide and N-hydroxysuccinimide gave BocPro-DTrp-Gly-DTrp-Leu-MetNH2 in 36% yield. De-t-butoxycarbonylation of BocPro-DTrp-Gly-DTrp-Leu-MetNH2 (0.68 g.) using trifluoroacetic acid in methyl ethyl sulfide and ethanedithiol gave HPro-DTrp-Gly-DTrp-Leu-MetNH2, which was isolated as the amorphous white solid phosphate (2:3) salt in 59% yield.

Sources & evidence

ORD record
ord-daf41efc11db48e987535baa8eed2e3c
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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