tert-Butyl bromoacetate → HCID 87460164, compound

HRID 2357958Notes

Reaction equation

HRID 2357958 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].O1CCCC1.[CH3:16][O:17][C:18]1[N:23]2[N:24]=[C:25]([C:27]([F:33])([F:32])[C:28]([F:31])([F:30])[F:29])[CH:26]=[C:22]2[C:21]([C:34](=[O:37])[CH2:35][CH3:36])=[CH:20][CH:19]=1.Br[CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41]>O1CCCC1>[CH3:16][O:17][C:18]1[N:23]2[N:24]=[C:25]([C:27]([F:33])([F:32])[C:28]([F:29])([F:30])[F:31])[CH:26]=[C:22]2[C:21]([C:34](=[O:37])[CH:35]([CH3:36])[CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 23714775LiHMDS tetrahydrofuranHCID 59389392HCID 59389392, compound

Product 1

HCID 87460164HCID 87460164, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In an argon atmosphere, a 1 mol/L lithium bis(trimethylsilyl)amide/tetrahydrofuran solution (4.14 mL) was added dropwise to a solution of the compound of Example 356 (1.16 g) in tetrahydrofuran (30 mL) at 0° C. The mixture was stirred at 0° C. for 20 min. Subsequently, t-butyl bromoacetate (0.797 mL) was added at 0° C. and the mixture was stirred at room temperature for 1 hour. The reaction was quenched by adding a saturated aqueous ammonium chloride solution and the mixture was extracted with ethyl acetate (200 mL). The extract was washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate. The extract was then concentrated and purified by silica gel column chromatography (hexane:ethyl acetate=2:1 v/v) to afford the title compound as a colorless powder (940 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. customThe reaction was quenched
  3. additionby adding a saturated aqueous ammonium chloride solution
  4. extractionthe mixture was extracted with ethyl acetate (200 mL)
  5. washThe extract was washed sequentially with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe extract was then concentrated
  8. custompurified by silica gel column chromatography (hexane:ethyl acetate=2:1 v/v)

Sources & evidence

ORD record
ord-488a4d51e4d5459997472ebd7cfe6977
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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