Citric Acid → HCID 58022576, compound

HRID 1517732Notes

Reaction equation

HRID 1517732 reaction equation
[C:1]([O:5][C:6]([NH:8][C@:9]([CH3:33])([CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)=[CH:17][C:16]=1[Cl:32])[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Br)(Br)(Br)Br.[P:39]([O:44]C)([O:42][CH3:43])[O:40][CH3:41].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>N1C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C@:9]([CH3:33])([CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:29])([F:30])[F:31])[CH:23]=2)=[CH:17][C:16]=1[Cl:32])[CH2:10][O:11][P:39]([O:42][CH3:43])([O:40][CH3:41])=[O:44])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8472Trimethyl phosphiteHCID 11205Carbon tetrabromideHCID 58022606HCID 58022606, compound

Product 1

HCID 58022576HCID 58022576, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of the compound of Example 16 (456 mg) in pyridine (5 mL) was added under ice cooling carbon tetrabromide (620 mg) and trimethyl phosphite (219 μL), and the resultant solution was then stirred at 0° C. for 1 hour. To the reaction solution was added 10% aqueous citric acid, extracted with ethyl acetate, washed with water and saturated brine in that order, and then dried over anhydrous sodium sulfate. The solvent was evaporated, and the resultant residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2) to obtain the target product (533 mg) as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water and saturated brine in that order
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe resultant residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-de75beef9c0d4c1e9fda7a0324162697
Source dataset
uspto-grants-2012_07
Patent number
US08232319B2

Reaction notes

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