Dicyclohexylcarbodiimide → HCID 178454226, compound

HRID 2226728Notes

Reaction equation

HRID 2226728 reaction equation
[N:1]1([C:30](OC(C)(C)C)=[O:31])[CH2:29][CH2:28][CH2:27][C@@H:2]1[C:3]([NH:5][C@H:6]([C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[NH:16])[NH:12][N+:13]([O-:15])=[O:14])=[O:4].Cl.CCOC(C)=O.[NH:44]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[C@H:45](C(O)=O)[CH2:46][O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CCN(CC)CC>[NH:44]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[C@H:45]([C:30]([N:1]1[CH2:29][CH2:28][CH2:27][C@@H:2]1[C:3]([NH:5][C@H:6]([C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[NH:16])[NH:12][N+:13]([O-:15])=[O:14])=[O:4])=[O:31])[CH2:46][O:47][CH2:48][C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1

Participants

7

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 21866389Hydrogen chloride-ethyl acetateHCID 178451950Boc-D-Pro-Arg(NO2)-OBzl

Product 1

HCID 178454226HCID 178454226, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The desired compound was prepared as an oily product from 12 g of Boc-D-Pro-Arg(NO2)-OBzl, 60 ml of 4 N HCl-AcOEt, 3.3 ml of Et3N, 7 g of Boc-Ser(Bzl)-OH, 4.2 g of HOBt and 5.1 g of DCC in the same manner as in Example 7-(2).

Sources & evidence

ORD record
ord-1044644fa47e4cfea3b3a16dc7a6ab86
Source dataset
uspto-grants-1994_09
Patent number
US05349050

Reaction notes

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