Dicyclohexylcarbodiimide → Z-Phe-His-Leu-Val 3-(m-carbamoylphenoxy)-2-hydroxypropyl amide

HRID 65360Notes

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]([C:52]1[CH:53]=[C:54]([CH:61]=[CH:62][CH:63]=1)[O:55][CH2:56][CH:57]([OH:60])[CH2:58][NH-:59])(=[O:51])[NH2:50].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]([C:52]1[CH:53]=[C:54]([CH:61]=[CH:62][CH:63]=1)[O:55][CH2:56][CH:57]([OH:60])[CH2:58][NH-:59])(=[O:51])[NH2:50]

Participants

Reactant 4

HCID 10868Dicyclohexylcarbodiimide

HCID 757711-Hydroxybenzotriazole

HCID 131714889HCID 131714889, compound

HCID 178523857Z-Phe-His-OH

Product 1

HCID 178445993Z-Phe-His-Leu-Val 3-(m-carbamoylphenoxy)-2-hydroxypropyl amide

Procedure

In a manner analogous to that described in Example 1, using as starting materials 77 mg of Z-Phe-His-OH, 37 mg of H-Leu-Val-3-(m-carbamoylphenoxy)- 2-hydroxypropyl amide, 27 mg of HOBt and 36 mg of DCCI, the title compound is obtained after flash chromatography (65 g of silica gel 60, 40-63 μm, eluant system B7). Rf (B7)=0.15, Rf (N12)=0.30.

Sources & evidence

ORD record: ord-8b69f0843db34615a3ce494cbb020f11
Source dataset: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04613676

Reaction notes

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