Water → HCID 86674673, compound

HRID 1261401Notes

Reaction equation

HRID 1261401 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([OH:22])[CH2:11][C:12]1([S:15]([O:18][CH:19]([CH3:21])[CH3:20])(=[O:17])=[O:16])[CH2:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23](Cl)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O.CC(OC)(C)C>CN(C=O)C.[Na+].[I-]>[CH2:23]([O:22][C@@H:10]([CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:11][C:12]1([S:15]([O:18][CH:19]([CH3:20])[CH3:21])(=[O:16])=[O:17])[CH2:13][CH2:14]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 15413tert-Butyl methyl etherHCID 89262141HCID 89262141, compound

Product 1

HCID 86674673HCID 86674673, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6228DimethylformamideSolvent3×

Procedure

Under a Nitrogen atmosphere was mixed NAH (91.5 g) in DMF (2 L) and (R)-isopropyl 1-(3-(benzyloxy)-2-hydroxypropyl)cyclopropane-1-sulfonate (715 g) in DMF (1 L) at a temperature between −5° C. and 5° C. for 140 minutes. After stirring for a further 5 minutes, NaI (5.1 g) was added. After BnCl (289.5 g) in DMF (300 mL) was added gradually, the reaction mixture was warmed slowly to room temperature and stirred for approximately 16 hours until HPLC analysis showed the reaction was complete. The reaction mixture was cooled to −5° C. and water (4 L) was added followed by MTBE (2 L (×2)) with stirring for 20 minutes. The organic layer was separated, washed with water (2 L (×2)), brine (2 L), dried over Na2SO4 and concentrated to give 830 g of product.

Workup

  1. stirringstirred for approximately 16 hours until HPLC analysis
  2. temperatureThe reaction mixture was cooled to −5° C.
  3. stirringwith stirring for 20 minutes
  4. customThe organic layer was separated
  5. washwashed with water (2 L (×2)), brine (2 L)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a1d4d912d5684ebabb0494a0e9adf172
Source dataset
uspto-grants-2013_06
Patent number
US08470878B2

Reaction notes

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