Ethyl Acetate → HCID 10414074, compound

HRID 1865811Notes

Reaction equation

HRID 1865811 reaction equation
[CH3:1][S:2]([O:5][CH2:6][CH2:7][N:8]([CH2:28][CH2:29]OS(C)(=O)=O)[C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([N+:18]([O-:20])=[O:19])=[CH:11][C:10]=1[C:21]([NH:23][CH2:24]CCO)=[O:22])(=[O:4])=[O:3].[Li+].[Br-:36].CCO[C:40]([CH3:42])=[O:41]>>[CH3:1][S:2]([O:5][CH2:6][CH2:7][N:8]([CH2:28][CH2:29][Br:36])[C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([N+:18]([O-:20])=[O:19])=[CH:11][C:10]=1[C:21]([NH:23][CH2:24][CH:40]([OH:41])[CH3:42])=[O:22])(=[O:4])=[O:3]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 82050Lithium BromideHCID 86610319HCID 86610319, compound

Product 1

HCID 10414074HCID 10414074, compound

Procedure

Treatment of 24 (0.25 g, 0.45 mmol) with LiBr (53 mg, 0.61 mmol) in EtOAc (50 mL) at 60° C. for 3 h, and chromatography of the product on silica gel, eluting with EtOAc/petroleum ether (from 2:1 to 1:0) gave IIb-13 (0.16 g, 66%): as yellow foam; 1H NMR [(CD3)2SO] δ 8.74 (d, J=2.8 Hz, 1 H), 8.73 (m, 1 H), 8.31 (d, J=2.8 Hz, 1 H), 4.28 (m, 2 H), 3.65-3.44 (m, 10 H), 3.13 (s, 3 H), 1.70 (m, 2 H); 13C NMR δ 165.1, 145.7, 145.4, 141.0, 136.2, 127.3, 122.1, 67.5, 58.4, 51.1, 36.7, 36.5, 31.7, 29.6. HRMS (FAB) Calcd. For C15H2279BrN4O9S [M+H+] m/z 513.0291. Found; 513.0281.

Workup

  1. washchromatography of the product on silica gel, eluting with EtOAc/petroleum ether (from 2:1 to 1:0)
  2. customgave IIb-13 (0.16 g, 66%)

Sources & evidence

ORD record
ord-fa82018d5a384370b95b76c462d3b599
Source dataset
uspto-grants-2009_12
Patent number
US07629332B2

Reaction notes

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