Citric Acid → HCID 59370448, compound

HRID 1685374Notes

Reaction equation

HRID 1685374 reaction equation
[CH:1]([N:4]1[C:9](=[O:10])[CH2:8][C@@H:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:6][C:5]1=[O:17])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:21][C:22]([O:24]C)=[O:23].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH:1]([N:4]1[C:9](=[O:10])[CH2:8][C@@H:7]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:6]([CH2:21][C:22]([OH:24])=[O:23])[C:5]1=[O:17])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 59370452HCID 59370452, compound

Product 1

HCID 59370448HCID 59370448, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (S)-3-isopropyl-6-phenyldihydropyrimidine-2,4(1H,3H)-dione from Step B (310 mg, 1.34 mmol) in THF (6 mL) at 0° C. was added NaH (45.0 mg of a 60% dispersion in oil, 1.87 mmol). After 15 min, methyl bromoacetate (0.202 mL, 2.14 mmol) was added and the mixture was stirred at ambient temperature for 16 h. NaOH (4.00 mL of a 1M solution) was added and the mixture was stirred at ambient temperature for 2 h. A 10% citric acid solution (20 mL) was added and the mixture was extracted with CH2Cl2 (3×20 mL). The combined CH2Cl2 extracts were dried over Na2SO4, filtered, and concentrated in vacuo to provide the title compound. MS: m/z=291 (M+1).

Workup

  1. stirringthe mixture was stirred at ambient temperature for 2 h
  2. extractionthe mixture was extracted with CH2Cl2 (3×20 mL)
  3. dry with materialThe combined CH2Cl2 extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-79b1cb0cd9b5434fad6fd188cc001360
Source dataset
uspto-grants-2012_04
Patent number
US08148390B2

Reaction notes

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