Ethyl bromoacetate → HCID 86761174, compound

HRID 1713560Notes

Reaction equation

HRID 1713560 reaction equation
Cl.[C:2]1([C:8]2([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:12]3[CH2:13][N:14]([C:17]([CH:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)=[O:18])[CH2:15][CH2:16][N:11]3[C:10](=[O:25])[O:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41]>O1CCCC1.O>[O:25]=[C:10]1[N:11]2[CH2:16][CH2:15][N:14]([C:17]([CH:19]3[CH2:24][CH2:23][N:22]([CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:21][CH2:20]3)=[O:18])[CH2:13][CH:12]2[C:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[O:9]1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 23121958HCID 23121958, compound

Product 1

HCID 86761174HCID 86761174, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of hexahydro-1,1-diphenyl-7-[(4-piperidinyl)carbonyl]-3H-oxazolo[3,4-a]pyrazin-3-one hydrochloride (0.20 g, 0.45 mmol) and potassium carbonate (0.16 g, 1.2 mmol) in tetrahydrofuran (5 mL) was added ethyl bromoacetate (0.055 mL, 0.50 mmol) at 0° C., and the mixture was stirred at 0° C. for 2 hours and at room temperature for 20 hours. The reaction solution was diluted with water and then extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solid was filtered off, and the filtrate was concentrated and dried to a solid. The residue was purified with silica gel column chromatography (ethyl acetate to ethyl acetate:methanol=9:1) to obtain the title compound (0.20 g, yield 90%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe solid was filtered off
  5. concentrationthe filtrate was concentrated
  6. customdried to a solid
  7. customThe residue was purified with silica gel column chromatography (ethyl acetate to ethyl acetate:methanol=9:1)

Sources & evidence

ORD record
ord-f5e9be64c1374ad38327d3e51b560bcc
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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