1,2-Dibromoethane → HCID 66615017, compound

HRID 2046045Notes

Reaction equation

[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:25])[NH:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Br[CH2:27][CH2:28]Br>CN(C=O)C>[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH2:28][CH2:27][N:17]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:16]2=[O:25])=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

Conditions

Temperature: -50 °C

Procedure

To a solution of the product of Example 11, Step A (0.05 g; 0.143 mmol) in anhydrous DMF (2 ml) 60% NaH in mineral oil (0.014 g; 0.344 mmol) was added at room temperature. After stirring for 1 h, to it 1,2-dibromoethane (0.172 ml; 0.2 mmol) was added. This was stirred at −50° C. for 1 h under N2, cooled to room and solvents were removed in vacuo. The residue was diluted to 15 ml with Et2O, washed with H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane/EtOAc 9.5:0.5) to give the title compound (0.02 g; 37%) as a colourless solid. 1H-NMR (CDCl3) 7.4 (d, 2H, J=8.5 Hz); 7.1 (d, 2H, J=8.5 Hz); 4.13 (q, 2H, J=7.1 Hz); 3.76 (m, 2H); 3.57 (t, 2H, J=6.7 Hz); 3.5 (m, 2H); 2.6 (t, 2H, J=6.7 Hz); 2.53 (t, 2H, J=7.9 Hz); 1.55 (m, 2H); 1.24 (m, 13H); 0.85 (t, 3H, J=6.9 Hz).

Workup

additionwas added
temperaturecooled to room and solvents
customwere removed in vacuo
additionThe residue was diluted to 15 ml with Et2O
washwashed with H2O, brine
dry with materialdried over anhydrous MgSO4
filtrationfiltered
customThe filtrate was evaporated under reduced pressure
customthe residue was purified by FCC (SiO2, hexane/EtOAc 9.5:0.5)

Sources & evidence

ORD record: ord-434ca456a09f467eb2afc4f79c16cbcf
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592399B2

Reaction notes

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