Hydrochloride 1,2-dimethoxyethane → H-His(DNP) 1(S)-cyclohexylmethyl-2(S)-hydroxy-5-(2-pyridyl)-pentylamide hydrochloride

HRID 1590758Notes

Reaction equation

HRID 1590758 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:21]([OH:23])=[O:22])[CH2:3][C:4]1[N:8]=[CH:7][N:6]([C:9]2[CH:20]=[CH:19][C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:10]=2[N+:11]([O-:13])=[O:12])[CH:5]=1.[CH:31]1([CH2:37][C@H:38]([NH-:50])[C@@H:39]([OH:49])[CH2:40][CH2:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.COCCOC.[ClH:57]>>[NH2:1][C@H:2]([C:21]([OH:23])=[O:22])[CH2:3][C:4]1[N:8]=[CH:7][N:6]([C:9]2[CH:20]=[CH:19][C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:10]=2[N+:11]([O-:13])=[O:12])[CH:5]=1.[ClH:57].[CH:31]1([CH2:37][C@H:38]([NH-:50])[C@@H:39]([OH:49])[CH2:40][CH2:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

3

Reactant 2

HCID 86628724Hydrochloride 1,2-dimethoxyethaneHCID 131717863Boc-His(DNP) 1(S)-cyclohexylmethyl-2(S)-hydroxy-5-(2-pyridyl)-pentylamide

Product 1

HCID 131717862H-His(DNP) 1(S)-cyclohexylmethyl-2(S)-hydroxy-5-(2-pyridyl)-pentylamide hydrochloride

Procedure

230 mg of Boc-His(DNP)-1(S)-cyclohexylmethyl-2(S)-hydroxy-5-(2-pyridyl)-pentylamide are stirred in 5 ml of saturated DME/HCl for 90 minutes and subsequently concentrated. 220 mg of the title compound are obtained as a resin.

Workup

  1. concentrationsubsequently concentrated

Sources & evidence

ORD record
ord-647e636cec69449d9d6c4cdcaf7ff393
Source dataset
uspto-grants-1993_04
Patent number
US05204357

Reaction notes

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