2,3-Butanediol → HCID 9968749, compound

HRID 1072672Notes

Reaction equation

HRID 1072672 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:25]=[CH:24][C:12]([O:13][CH:14]([CH3:23])[CH2:15][NH:16][S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[Na+].[Na+].BrC1C=CC(O[C@H](C)CNS(C(C)C)(=O)=O)=CC=1.CC(O)C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:23][C@@H:14]([O:13][C:12]1[CH:24]=[CH:25][C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)=[CH:10][CH:11]=1)[CH2:15][NH:16][S:17]([CH:20]([CH3:21])[CH3:22])(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 2622,3-ButanediolHCID 10340Sodium CarbonateHCID 9841733HCID 9841733, compoundHCID 59120936HCID 59120936, compound

Product 1

HCID 9968749HCID 9968749, compoundYield 113%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
85 °C

Procedure

4-Cyanobenzeneboronic acid (171 mg, 1.16 mmol, prepared in example 25), tetrakis(triphenylphosphine)palladium(0) (69 mg, 0.063 mmol), 2 M sodium carbonate (1.6 mL), and [(2R)-2-(4-bromophenoxy)propyl][(methylethyl)sulfonyl]amine (310 mg, 0.922 mmol) were combined in a 15 mL round bottomed flask with dimethylethylene glycol (6.15 mL, DME), fitted with a condenser, stirbar, and in a temperature regulated oil bath, and refluxed in a nitrogen system to 85° C., overnight. The reaction was allowed to cool to room temperature, and quenched with 15 mL of water, and extracted three times with 15 mL ethyl acetate. The organic layer was dried with magnesium sulfate, filtered through Celite®, and concentrated under reduced pressure, yielding 470 mg viscous black oil. This material was further purified using a 4000 uM rotor on a Chromatotron® in a 1:1 hexanes:ethyl acetate solvent system yielding the final title compound (57.5 mg, 18%) as white crystals.

Workup

  1. customfitted with a condenser
  2. temperatureto cool to room temperature
  3. customquenched with 15 mL of water
  4. extractionextracted three times with 15 mL ethyl acetate
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. filtrationfiltered through Celite®
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cb0c7fc48d4343c693a0f569d7b16213
Source dataset
uspto-grants-2005_06
Patent number
US06911476B2

Reaction notes

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