Dicyclohexylcarbodiimide → HCID 178451006, compound

HRID 65355Notes

Reaction equation

[NH:1]([C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[C@H:2]([C:10]([NH:12][C@H:13]([C:20](O)=[O:21])[CH2:14][C:15]1[N:19]=[CH:18][NH:17][CH:16]=1)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:33][C@H:34]([C:39]([NH:41][C@H:42]([C:46]([OH:48])=[O:47])[CH:43]([CH3:45])[CH3:44])=[O:40])[CH2:35][CH:36]([CH3:38])[CH3:37].[C:49]([O:53][C:54]([CH2:56][CH2:57][CH2:58][CH2:59][NH-:60])=[O:55])([CH3:52])([CH3:51])[CH3:50].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>>[NH:1]([C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[C@H:2]([C:10]([NH:12][C@H:13]([C:20]([NH:33][C@H:34]([C:39]([NH:41][C@H:42]([C:46]([OH:48])=[O:47])[CH:43]([CH3:44])[CH3:45])=[O:40])[CH2:35][CH:36]([CH3:37])[CH3:38])=[O:21])[CH2:14][C:15]1[N:19]=[CH:18][NH:17][CH:16]=1)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:49]([O:53][C:54]([CH2:56][CH2:57][CH2:58][CH2:59][NH-:60])=[O:55])([CH3:52])([CH3:51])[CH3:50]

Participants

Reactant 4

HCID 10868Dicyclohexylcarbodiimide

HCID 757711-Hydroxybenzotriazole

HCID 131714880HCID 131714880, compound

HCID 178523857Z-Phe-His-OH

Product 1

HCID 178451006HCID 178451006, compound

Procedure

In a manner analogous to that described in Example 1, using as starting materials 144 mg of Z-Phe-His-OH, 138 mg of H-Leu-Val-4-tert.-butoxycarbonylbutyl amide, 51 mg of HOBt and 89 mg of DCCI, the title compound is obtained after flash chromatography (180 g of silica gel 60, 40-63 μm, system N10). Rf (B2)=0.40, Rf (N8)=0.41.

Sources & evidence

ORD record: ord-ceea1944dd2b4766971775c7ec98f663
Source dataset: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04613676

Reaction notes

Loading…