Bis(2-bromoethyl) ether → HCID 178514730, compound

HRID 1043245Notes

Reaction equation

HRID 1043245 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:12][C:11]=2[N+:20]([O-:22])=[O:21])[CH2:4][CH2:3]1.C(N(C(C)C)CC)(C)C.Br[CH2:33][CH2:34][O:35][CH2:36][CH2:37]Br>CN(C)C=O.C(OCC)(=O)C>[O:35]1[CH2:36][CH2:37][N:1]([C@H:2]2[CH2:3][CH2:4][C@H:5]([CH2:8][NH:9][C:10]3[CH:15]=[CH:14][C:13]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:12][C:11]=3[N+:20]([O-:22])=[O:21])[CH2:6][CH2:7]2)[CH2:33][CH2:34]1

Participants

6

Reactant 3

HCID 21521Bis(2-bromoethyl) etherHCID 81531DiisopropylethylamineHCID 178514731HCID 178514731, compound

Product 1

HCID 178514730HCID 178514730, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of EXAMPLE 451B (0.85 g) and diisopropylethylamine (2.03 mL) in N,N-dimethylformamide (7 mL) was added bis(2-bromoethyl)ether (0.54 g) as a solution in N,N-dimethylformamide (1 mL). The reaction was stirred at room temperature for 1 hour and heated to 70° C. overnight. The reaction was cooled, diluted with ethyl acetate (100 mL), washed with water (50 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography (Revleris 120 g) eluting with a gradient of 0.75% to 7.5% over 30 minutes (flow=80 ml/min) gave the title compound.

Workup

  1. temperatureheated to 70° C. overnight
  2. temperatureThe reaction was cooled
  3. washwashed with water (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washSilica gel chromatography (Revleris 120 g) eluting with a gradient of 0.75% to 7.5% over 30 minutes (flow=80 ml/min)

Sources & evidence

ORD record
ord-35ef4806a64f433d94b0a939db405223
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Reaction notes

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