Ethyl bromoacetate → HCID 67016579, compound

HRID 1623084Notes

Reaction equation

HRID 1623084 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13](=[O:14])[NH:12][CH2:11][CH2:10][N:9]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CN(C=O)C>[CH2:29]([O:28][C:26](=[O:27])[CH2:25][N:12]1[CH2:11][CH2:10][N:9]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:13]1=[O:14])[CH3:30]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 58044818HCID 58044818, compound2×

Product 1

HCID 67016579HCID 67016579, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (±)-tert-butyl 2-(4-fluorophenyl)-3-oxopiperazine-1-carboxylate (50.0 mg, 0.170 mmol, described in Intermediate 48) and sodium hydride (8.15 mg, 0.204 mmol, 60% dispersion in mineral oil) in DMF (1 mL) was stirred at ambient temperature for 0.5 h. Ethyl bromoacetate (0.023 mL, 0.204 mmol) was added and stirring continued for 16 h. The reaction mixture was purified by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. The pure, product-containing fractions were neutralized with saturated aqueous NaHCO3 (10 mL) and extracted with CH2Cl2 (3×10 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: m/z=381 (M+1).

Workup

  1. customThe reaction mixture was purified by HPLC
  2. washeluting with a gradient of H2O
  3. additionThe pure, product-containing fractions
  4. extractionextracted with CH2Cl2 (3×10 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-db112aefda734b8c8220e648ee2e1510
Source dataset
uspto-grants-2014_07
Patent number
US08778957B2

Reaction notes

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