Dicyclohexylcarbodiimide → HCID 178462154, compound

HRID 1196295Notes

Reaction equation

HRID 1196295 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:4]([N:6]1[CH2:34][CH2:33][CH2:32][C@H:7]1[C:8]([NH:10][C@H:11]([C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[CH2:12][CH2:13][CH2:14][NH:15][C:16](=[NH:21])[NH:17][N+:18]([O-:20])=[O:19])=[O:9])=[O:5])[CH3:3].Cl.CCOC(C)=O.[NH:49]([C:58]([O:60][CH2:61][C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)=[O:59])[C@H:50]([C:55]([OH:57])=O)[CH2:51][C:52](=[O:54])[NH2:53].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>>[NH:49]([C:58]([O:60][CH2:61][C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)=[O:59])[C@H:50]([C:55]([NH:1][C@H:2]([C:4]([N:6]1[CH2:34][CH2:33][CH2:32][C@H:7]1[C:8]([NH:10][C@H:11]([C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])[CH2:12][CH2:13][CH2:14][NH:15][C:16](=[NH:21])[NH:17][N+:18]([O-:20])=[O:19])=[O:9])=[O:5])[CH3:3])=[O:57])[CH2:51][C:52](=[O:54])[NH2:53]

Participants

6

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 75314Benzyloxycarbonyl-asparagineHCID 757711-HydroxybenzotriazoleHCID 21866389Hydrogen chloride-ethyl acetateHCID 178462202HCID 178462202, compound

Product 1

HCID 178462154HCID 178462154, compound

Procedure

The desired compound was prepared from 2.9 g of Boc-Ala-Pro-Arg(NO2)-OBzl, 15 ml of 4N HCl-AcOEt, 1.4 g of Z-Asn-OH, 1.0 g of HOBt and 1.1 g of DCC in the same manner as in Example 7-(3).

Sources & evidence

ORD record
ord-5637d9363cfa4f14a3f6f08519974df1
Source dataset
uspto-grants-1992_05
Patent number
US05112947

Reaction notes

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