Sodium Hydroxide → HCID 23122089, compound

HRID 1713535Notes

Reaction equation

HRID 1713535 reaction equation
C([N:3]([C:8]([N:10]1[CH2:15][CH2:14][N:13]2[C:16](=[O:31])[O:17][C:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:12]2[CH2:11]1)=[O:9])[CH2:4][C:5]([OH:7])=[O:6])C.[OH-].[Na+]>C(O)C.O1CCCC1>[O:31]=[C:16]1[N:13]2[CH2:14][CH2:15][N:10]([C:8]([NH:3][CH2:4][C:5]([OH:7])=[O:6])=[O:9])[CH2:11][CH:12]2[C:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:17]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68421596HCID 68421596, compound

Product 1

HCID 23122089HCID 23122089, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl N-[(tetrahydro-3-oxo-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-7(1H)-yl)carbonyl]glycine (1.5 g, 3.6 mmol) was dissolved in ethanol (10 mL) and tetrahydrofuran (2 mL). With ice cooling, a 4 M aqueous sodium hydroxide solution (1.0 mL, 4.0 mmol) was added thereto, and the mixture was stirred at 0° C. for 3 hours. The reaction solution was concentrated under reduced pressure, and diethyl ether and water were added to the residue. The aqueous layer was neutralized with 4 M hydrochloric acid, which was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and hexane was added to the residue. The resulting mixture was powdered and dried to obtain the title compound (1.2 g, yield 84%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, and diethyl ether and water
  2. additionwere added to the residue
  3. extractionwas extracted with ethyl acetate
  4. concentrationThe organic layer was concentrated under reduced pressure, and hexane
  5. additionwas added to the residue
  6. customdried

Sources & evidence

ORD record
ord-73db9fd5614d4ab3989ed4ae8c10b5db
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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