Citric Acid → HCID 18630161, compound

HRID 378027Notes

Reaction equation

HRID 378027 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-246323ff0d6b45099ffce67e25c9f2b7
Source dataset
uspto-grants-2000_02
Patent number
US06028101

Reaction notes

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