Water → HCID 66681368, compound

HRID 1964514Notes

Reaction equation

HRID 1964514 reaction equation
[OH:1][CH:2]([C:5]1[N:6]=[C:7]([C:10]2[N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:12]=[CH:13][CH:14]=2)[S:8][CH:9]=1)[CH2:3][OH:4].[Br:22]N1C(=O)CCC1=O.O>O1CCCC1>[Br:22][C:12]1[N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]([C:7]2[S:8][CH:9]=[C:5]([CH:2]([OH:1])[CH2:3][OH:4])[N:6]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 66683297HCID 66683297, compound

Product 1

HCID 66681368HCID 66681368, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

t-Butyl 2-[4-(1,2-dihydroxyethyl)-1,3-thiazol-2-yl]-1H-pyrrole-1-carboxylate (868 mg, 2.80 mmol) synthesized in Example (9c) was dissolved in tetrahydrofuran (30 mL), and cooled to 0° C. N-Bromosuccinimide (498 mg, 2.80 mmol) was added, and stirring was carried out at room temperature for 14 hours under nitrogen atmosphere. Water (20 mL) was added, and extraction was carried out with diethyl ether (20 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=0%-30%) to afford the desired compound (527 mg, yield 48%) as a pale yellow oil.

Workup

  1. extractionextraction
  2. washThe organic layer was washed with saturated brine
  3. dry with materialsubsequently dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=0%-30%)

Sources & evidence

ORD record
ord-1bd398cb371e4a1390edb606621c6293
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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