Chlorosuccinimide → HCID 86592441, compound

HRID 1795300Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:26])[CH2:5][N:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH:12][C@H:13]([CH2:21][N:22]=[N+:23]=[N-:24])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]1=[O:25])[CH3:2].[Cl:27]N1C(=O)CCC1=O>ClC(Cl)C>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][N:6]1[C:11]([Cl:27])=[CH:10][N:9]=[C:8]([NH:12][C@H:13]([CH2:21][N:22]=[N+:23]=[N-:24])[CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:7]1=[O:25])[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of (S)-[3-(1-azidomethyl-2-phenyl-ethylamino)-2-oxo-2H-pyrazin-1-yl]-acetic acid ethyl ester (5.8 g, 16.3 mmol) in dichloroethane (90 ml) was added N-chlorosuccinimide (2.17 g, 16.3 mmol) and the reaction mixture was stirred at 85° C. for 1 h 30 and at room temperature for 18 h. The reaction mixture was concentrated in vacuo and purified by flash chromatography (silica gel, 20% diethyl ether in hexane to 45%) to give (S)-[3-(1-azidomethyl-2-phenyl-ethylamino)-6-chloro-2-oxo-2H-pyrazin-1-yl]-acetic acid ethyl ester as a thick syrup. 1H NMR (CDCl3, 400 MHz): δ 7.38–7.20 (m, 5H); 6.85 (s, 1H); 6.10 (bd, J=8.8 Hz,1H); 4.92 (A of AB, d, J=17.7 Hz, 1H));); 4.86 (B of AB, d, J=17.7 Hz, 1H)); 4.40–4.30 (m, 1H); 4.25 (q, J=7 Hz, 2H); 3.52 (A of ABX, dd, J=12.4, 4.6 Hz, 1H); 3.40 (B of ABX, dd, J=12.4, 4.6 Hz, 1H); 3.00 (A of ABX, dd, J=13.5, 6.4 Hz, 1H); 2.92 (B of ABX, dd, J=13.5, 7.4 Hz, 1H); 1.29 (t, J=7 Hz, 3H).

Workup

waitat room temperature for 18 h
concentrationThe reaction mixture was concentrated in vacuo
custompurified by flash chromatography (silica gel, 20% diethyl ether in hexane to 45%)

Sources & evidence

ORD record: ord-8e2f6754aa34499da00a40643d73b04a
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07026324B2

Reaction notes

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