N-bromobutanimide → HCID 66968760, compound

HRID 1255528Notes

Reaction equation

HRID 1255528 reaction equation
[CH:1]1([C@H:6]2[C:31](=[O:32])[N:30]3[CH2:33][C@@H:27]([CH2:28][C@H:29]3[C:34]([O:36][CH3:37])=[O:35])[O:26][C:25]3[N:20]([C:21](=[O:38])[CH:22]=[CH:23][CH:24]=3)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]3[C@@H:10]([CH2:11][CH2:12][CH2:13]3)[O:9][C:8](=[O:39])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1C(=O)N([Br:47])C(=O)C1>C(#N)C>[Br:47][C:22]1[C:21](=[O:38])[N:20]2[C:25]([O:26][C@H:27]3[CH2:33][N:30]([C:31](=[O:32])[C@H:6]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)[NH:7][C:8](=[O:39])[O:9][C@H:10]4[C@H:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[CH2:13][CH2:12][CH2:11]4)[C@H:29]([C:34]([O:36][CH3:37])=[O:35])[CH2:28]3)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 66969198HCID 66969198, compound

Product 1

HCID 66968760HCID 66968760, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 25 mL round bottom flask under nitrogen was charged with the product of Example 82 Step 1 (238 mg, 0.438 mmol), NBS (39.0 mg, 0.219 mmol), and acetonitrile (15 ml). Stirred at room temperature 10 minutes. HPLC/MS shows mainly desired; little starting material. Added an additional 10 mg NBS. Still a little starting material remaining. Added another 10 mg NES. HPLC/MS looks good. Cooled. Evaporated. Subjected to ISCO chromatography eluting with a hexane/ethyl acetate gradient. Evaporated fractions containing product to give the title compound as a white solid. (224 mg, 0.360 mmol, 82% yield). LCMS (ES+) m/z 623.3 (M+H)+.

Workup

  1. additionAdded another 10 mg NES
  2. temperatureCooled
  3. customEvaporated
  4. washeluting with a hexane/ethyl acetate gradient
  5. additionEvaporated fractions containing product

Sources & evidence

ORD record
ord-5d5f131436064916ad10ab226562b490
Source dataset
uspto-grants-2013_06
Patent number
US08461107B2

Reaction notes

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