Bromoacetic Acid → HCID 58513728, compound

HRID 2362724Notes

Reaction equation

HRID 2362724 reaction equation
[H-].[Na+].[OH:3][C:4]1([C:16]2[S:17][CH:18]=[CH:19][N:20]=2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5]1.Br[CH2:22][C:23]([OH:25])=[O:24]>CN(C)C=O>[C:12]([O:11][C:9]([N:6]1[CH2:7][CH2:8][C:4]([C:16]2[S:17][CH:18]=[CH:19][N:20]=2)([O:3][CH2:22][C:23]([OH:25])=[O:24])[CH2:5]1)=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 6227Bromoacetic AcidHCID 24758Sodium hydrideHCID 59298225HCID 59298225, compound

Product 1

HCID 58513728HCID 58513728, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To an ambient suspension of NaH (5.40 g, 135 mmol) in N,N-dimethylformamide (50 mL) was added dropwise a solution of tert-butyl 3-hydroxy-3-(thiazol-2-yl)pyrrolidine-1-carboxylate (7.30 g, 27 mmol) in N,N-dimethylformamide (20 mL). After 30 minutes, bromoacetic acid (7.50 g, 54.0 mmol) in N,N-dimethylformamide (20 mL) was added dropwise. The solution was stirred at room temperature for 16 hours and then heated to 50° C. for 3 hours. The reaction was cooled to room temperature and was quenched by the addition of water. The solution was basicified to pH 10 by the addition of 2.5 M NaOH solution. The aqueous layer was extracted with ether, and the organics discarded. The aqueous layer was acidified to pH 1 with 6 M HCl solution, and then extracted with ethyl acetate (2×). The combined organics were washed with water, brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the product. MS ESI(+) m/z 329.3 [M+H]+.

Workup

  1. temperatureheated to 50° C. for 3 hours
  2. temperatureThe reaction was cooled to room temperature
  3. customwas quenched by the addition of water
  4. additionThe solution was basicified to pH 10 by the addition of 2.5 M NaOH solution
  5. extractionThe aqueous layer was extracted with ether
  6. extractionextracted with ethyl acetate (2×)
  7. washThe combined organics were washed with water, brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto give the product

Sources & evidence

ORD record
ord-f7f12429430a43caa76acfd4831f834f
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

Loading…