Citric Acid → HCID 18630161, compound

HRID 610918Notes

Reaction equation

HRID 610918 reaction equation
Br[C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([Si:18]([CH3:21])([CH3:20])[CH3:19])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13])=[O:5].C1COCC1.[Li]C(CC)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1CCCCC1>[CH3:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[NH:6][C:4](=[O:5])[C:3]1[CH:2]=[CH:17][CH:16]=[CH:15][C:14]=1[Si:18]([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 18630160HCID 18630160, compoundHCID 178418400CID 53628100

Product 1

HCID 18630161HCID 18630161, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

The compound of Example 120 (0.0021 mol, 0.75 g) and 50 mL THF were cooled to -78° C. in a nitrogen atmosphere with magnetic stirring. 1.3M s-BuLi (0.0026 mol, 2 mL) in cyclohexane was added dropwise. After stirring for 30 min, 25 mL of 25% citric acid were added. The mixture was then extracted three times with ethyl acetate, the extracts combined and washed with brine and twice with water, dried (MgSO4) and concentrated. The title compound was recrystallized as a white solid from ethyl acetate/hexanes in 54% yield. m.p. 117-119° C.

Workup

  1. extractionThe mixture was then extracted three times with ethyl acetate
  2. washwashed with brine and twice with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe title compound was recrystallized as a white solid from ethyl acetate/hexanes in 54% yield

Sources & evidence

ORD record
ord-a746049019b44a398d10eea69805cf97
Source dataset
uspto-grants-1999_12
Patent number
US05998466

Reaction notes

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