Ethyl acetimidate → HCID 178465613, compound

HRID 1952733Notes

Reaction equation

HRID 1952733 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]1([CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:37])[C@H:19]([CH2:33][CH2:34][CH2:35][NH2:36])[N:20]([C:29](=[O:32])[CH2:30][NH2:31])[CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:38](=[NH:43])(OCC)[CH3:39]>C(O)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]1([CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:37])[C@H:19]([CH2:33][CH2:34][CH2:35][NH2:36])[N:20]([C:29](=[O:32])[CH2:30][NH:31][C:38](=[NH:43])[CH3:39])[CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 65066Ethyl acetimidateHCID 86757013HCID 86757013, compound

Product 1

HCID 178465613HCID 178465613, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Glycyl-Nα-(phenethyl)omithine 3-phenylpropylamide trifluoroacetate was treated with ethyl acetimidate in ethanol at pH9 and the product was purified by HPLC: 1H NMR (400 MHz, D2O) δ 1.6-2.0 (m, 6 H), 2.3 (s, 3 H), 2.7 (t, J=6.4 Hz, 2 H), 2.9-3.1 (m, 4 H), 3.2-3.4 (m, 2 H), 3.5-3.7 (m, 2 H), 4.1-4.3 (m, 2 H), 4.7-4.8 (m, 1 H), and 7.2-7.5 (m, 10 H); mass spectrum, m/e 453 (M+), 354, 300, 247, and 219.

Workup

  1. customthe product was purified by HPLC

Sources & evidence

ORD record
ord-4098c41c7f3b4df09d5a502c37927682
Source dataset
uspto-grants-2000_09
Patent number
US06114310

Reaction notes

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