Benzoyl chloride → HCID 67303732, compound

HRID 1819711Notes

Reaction equation

HRID 1819711 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C@:5]([OH:16])([CH3:15])[C@@H:6]([C@H:8]1[CH2:12][O:11][C:10]([CH3:14])([CH3:13])[O:9]1)[OH:7])[CH3:2].[C:18](Cl)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19]>N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:17])[C@:5]([OH:16])([CH3:15])[C@@H:6]([C@H:8]1[CH2:12][O:11][C:10]([CH3:13])([CH3:14])[O:9]1)[O:7][C:18](=[O:19])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:2]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 52987879ethyl (2S,3R)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,3-dihydroxy-2-methylpropanoate

Product 1

HCID 67303732HCID 67303732, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of compound 42 (245 mg, 0.99 mmol) in dry pyridine (3 mL) is added dropwise a solution of BzCl (300 mg, 2.1 mmol) in pyridine (1 mL). After the mixture is stirred at room temperature for 2 h, the reaction is quenched with H2O (1 mL). The mixture is concentrated to dryness and the residue is partitioned between CH2Cl2 and sat. NaHCO3 solution. The organic phase is dried (anh. Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography with 5% EtOAc in hexanes to give 43 (247 mg, 71%) as a solid. Anal. Calcd for C18H24O7: C, 61.35; H, 6.86. Found: C, 60.95; H, 6.73.

Workup

  1. customthe reaction is quenched with H2O (1 mL)
  2. concentrationThe mixture is concentrated to dryness
  3. customthe residue is partitioned between CH2Cl2 and sat. NaHCO3 solution
  4. dry with materialThe organic phase is dried (anh. Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by silica gel column chromatography with 5% EtOAc in hexanes

Sources & evidence

ORD record
ord-5d76f1fad2d446bc898f0a0e751d2cc3
Source dataset
uspto-grants-2009_10
Patent number
US07601820B2

Reaction notes

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