N-bromobutanimide → HCID 59807072, compound

HRID 1922444Notes

Reaction equation

[N:1]1([CH:12]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]2)[CH2:7][CH2:6][CH2:5][CH2:4][C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.[Br:24]N1C(=O)CCC1=O>CN(C=O)C.O>[Br:24][C:9]1[CH:10]=[CH:11][C:2]2[N:1]([CH:12]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]3)[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=2[CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of compound 2 (3.15 g, 9.97 mmol) in DMF (15 mL) was cooled to 0° C. and treated drop wise with a solution of N-bromosuccinimide (1.77 g, 9.97 mmol) in DMF (15 mL). The reaction mixture was stirred at 0° C. for 3 hours then diluted with H2O (100 mL) and extracted into EtOAc (2×100 mL). The combined organic fractions were washed with brine (100 mL), dried (Na2SO4) and concentrated. The crude product was purified by column chromatography (EtOAc:hexanes, 1:9) to obtain compound 3 (3.26 g, 83%) as a foam. 1H NMR (DMSO-d6) δ 1.38 (s, 9H), 1.41-1.52 (m, 5H), 1.80-1.87 (m, 1H), 2.12-2.17 (m, 1H), 2.65-2.69 (m, 2H), 2.79-2.92 (m, 2H), 3.00-3.08 (m, 1H), 3.15-3.25 (m, 1H), 3.53-3.59 (m, 1H), 3.96-4.04 (m, 1H), 6.93-6.96 (d, 1H, J=8.4 Hz), 7.23 (dd, 1H, J=2.4, 8.4 Hz), 7.29 (d, 1H, J=2.4 Hz); ESI-MS (m/z, %): 395 (MH+, 7), 341 (92), 339 (100).

Workup

extractionextracted into EtOAc (2×100 mL)
washThe combined organic fractions were washed with brine (100 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe crude product was purified by column chromatography (EtOAc:hexanes, 1:9)

Sources & evidence

ORD record: ord-c908f11f76cc403296f3e0941698a761
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173813B2

Reaction notes

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