Citric Acid → HCID 59302382, compound

HRID 2237377Notes

Reaction equation

HRID 2237377 reaction equation
[Cl-].[Li+].[BH4-].[Na+].C[O:6][C:7](=O)[C@H:8]([CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.O.C(O)C>[CH2:13]([O:12][C:10]([NH:9][C@H:8]([CH2:7][OH:6])[CH2:20][Si:21]([CH3:22])([CH3:23])[CH3:24])=[O:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 311Citric AcidHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 59302364HCID 59302364, compound

Product 1

HCID 59302382HCID 59302382, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium chloride (0.64 g, 15 mmol) and sodium borohydride (0.57 g, 15 mmol) and then ethanol (22 ml) are added to a solution of example 74A (2.32 g, 7.5 mmol) in THF (14 ml). The mixture is stirred at RT overnight. For the workup, the mixture is adjusted to pH 4 with a citric acid solution (10% in water) while cooling with ice water, then diluted with 200 ml of water and extracted three times with dichloromethane. The combined organic phases are dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is separated by means of HPLC (Method 41) and the suitable fractions are concentrated in vacuo. The title compound is obtained as an oil (1.24 g, 59% of theory).

Workup

  1. extractionextracted three times with dichloromethane
  2. dry with materialThe combined organic phases are dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is separated by means of HPLC (Method 41)
  6. concentrationthe suitable fractions are concentrated in vacuo

Sources & evidence

ORD record
ord-7202189ea56f4cc386b4ebb8d1e59149
Source dataset
uspto-grants-2010_05
Patent number
US07718611B2

Reaction notes

Loading…