Dichloromethane → HCID 66797949, compound

HRID 447659Notes

Reaction equation

HRID 447659 reaction equation
C([O-])(=O)C.[Pb+4].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Cl:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[C@@H:24]([NH:28][C@H](C1C=CC=CC=1)CO)[CH2:23][C:22]2([CH3:39])[CH3:38].C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>CO.O>[ClH:18].[Cl:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[C@@H:24]([NH2:28])[CH2:23][C:22]2([CH3:39])[CH3:38]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 66797682HCID 66797682, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 66797949HCID 66797949, compoundYield 171.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of lead(IV) acetate (9.92 g, 0.0212 mol) in methanol (80 mL) at 0° C. under an atmosphere of nitrogen was added (2R)-2-{[(1S)-5-chloro-3,3-dimethyl-2,3-dihydro-1H-inden-1-yl]amino}-2-phenylethanol (4.288 g, 0.01358 mol) as a solution in methanol (80 mL) dropwise over 10 min. On completion of the addition, the mixture was warmed to 23° C. and stirred for 90 mins. To this was added 0.943 M of sodium carbonate in water (194 mL) and the mixture stirred for 10 min. CH2Cl2 (500 mL) was added and the mixture was filtered and washed with CH2Cl2. The filtrates were collected, the organic phase was separated and the aqueous extracted with CH2Cl2 (25 ml). The combined organics were evaporated to dryness. The residue was dissolved in ethanol (500 mL) and 10.4 M of hydrochloric acid in water (15.6 mL) was added. The mixture was heated to reflux (95° C.) overnight. The mixture was cooled, evaporated and the residue was treated with ether and sonicated. The solid was isolated by filtration, washed with ether and dried to yield the title compound (2.704 g, 86%) as the HCl salt.

Workup

  1. additionOn completion of the addition
  2. stirringthe mixture stirred for 10 min
  3. filtrationthe mixture was filtered
  4. washwashed with CH2Cl2
  5. customThe filtrates were collected
  6. customthe organic phase was separated
  7. extractionthe aqueous extracted with CH2Cl2 (25 ml)
  8. customThe combined organics were evaporated to dryness
  9. dissolutionThe residue was dissolved in ethanol (500 mL)
  10. addition10.4 M of hydrochloric acid in water (15.6 mL) was added
  11. temperatureThe mixture was heated
  12. temperatureto reflux (95° C.) overnight
  13. temperatureThe mixture was cooled
  14. customevaporated
  15. additionthe residue was treated with ether
  16. customsonicated
  17. customThe solid was isolated by filtration
  18. washwashed with ether
  19. customdried

Sources & evidence

ORD record
ord-aff75fdfef9d4471a0b0fc0ebc54b778
Source dataset
uspto-grants-2013_07
Patent number
US08481550B2

Reaction notes

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