3,4-dihydro-2H-pyran → HCID 70270372, compound

HRID 2289371Notes

Reaction equation

HRID 2289371 reaction equation
[OH:1][C@H:2]([CH2:6][C@@H:7]([CH3:12])[CH2:8][CH2:9][CH2:10][CH3:11])[C:3]([NH2:5])=[O:4].[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1.C(=O)([O-])O.[Na+]>C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)C>[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[O:1][C@H:2]([CH2:6][C@@H:7]([CH3:12])[CH2:8][CH2:9][CH2:10][CH3:11])[C:3]([NH2:5])=[O:4]

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 57183489HCID 57183489, compound

Product 1

HCID 70270372HCID 70270372, compoundYield 67.4%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 3283Diethyl EtherSolvent

Procedure

In a flask were charged 3.5 g of (2R,4S)-2-hydroxy-4-methylcaprylic amide synthesized in Step 5, 2.21 g of 3,4-dihydropyran, 50 ml of diethyl ether, and 0.1 g of p-toluenesulfonic acid at room temperature, and the mixture was stirred at room temperature overnight. The reaction mixture was poured into 100 ml of a 1% sodium hydrogencarbonate aqueous solution and extracted with diethyl ether. The extract was washed with water and concentrated to obtain 6.6 g of a crude product, which was then purified by silica gel column chromatography to obtain 3.5 g (67.4%) of the titled compound.

Workup

  1. extractionextracted with diethyl ether
  2. washThe extract was washed with water
  3. concentrationconcentrated
  4. customto obtain 6.6 g of a crude product, which
  5. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bed0457c4e364fd289e806560856107c
Source dataset
uspto-grants-2000_07
Patent number
US06093345

Reaction notes

Loading…