Stannous Chloride → HCID 58619021, compound

HRID 1795301Notes

Reaction equation

HRID 1795301 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][N:6]1[C:11]([Cl:12])=[CH:10][N:9]=[C:8]([NH:13][C@H:14]([CH2:22][N:23]=[N+]=[N-])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:7]1=[O:26])[CH3:2].Cl[Sn]Cl>CO.C1COCC1>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][N:6]1[C:11]([Cl:12])=[CH:10][N:9]=[C:8]([NH:13][C@H:14]([CH2:22][NH2:23])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:7]1=[O:26])[CH3:2]

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 86592441HCID 86592441, compound

Product 1

HCID 58619021HCID 58619021, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-[3-(1-azidomethyl-2-phenyl-ethylamino)-6-chloro-2-oxo-2H-pyrazin-1-yl]-acetic acid ethyl ester (5.67 g, 14.5 mmol) in MeOH (80 ml) and THF (40 ml) was added SnCl2 (4.1 g, 21.8 mmol) and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated in vacuo, azeotroped with CH2Cl2, and purified by flash chromatography (silica gel, 6% MeOH containing 10% NH4OH in CH2Cl2 to 10%) to give (S)-[3-(1-aminomethyl-2-pheny-ethylamino)-6-chloro-2-oxo-2H-pyrazin-1-yl]-acetic acid ethyl ester as a beige solid. 1H NMR (CDCl3, 400 MHz): δ 7.35–7.15 (m, 5H); 6.92 (s, 1H); 6.17 (bd, J=8.5 Hz, 1H); 4.88 (s, 2H));); 4.35–4.15(m, 3H); 3.00–2.70 (m, 4H); 1.32 (t, J=6.9 Hz, 3 H); rotation: [α]d=−82.6° (c=0.42, MeOH).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customazeotroped with CH2Cl2
  3. custompurified by flash chromatography (silica gel, 6% MeOH containing 10% NH4OH in CH2Cl2 to 10%)

Sources & evidence

ORD record
ord-30912385684c422eb652c3690b464656
Source dataset
uspto-grants-2006_04
Patent number
US07026324B2

Reaction notes

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