Sodium Sulfate → HCID 58071963, compound

HRID 715697Notes

Reaction equation

HRID 715697 reaction equation
C([C@@H]1CC[C@@H](C)C[C@H]1[O:11][C:12]([C@H:14]1[CH2:18][N:17]([C@@H:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:20])[C:16](=[O:27])[N:15]1S(C1C=CC(C)=CC=1)(=O)=O)=O)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[OH:11][CH2:12][C@H:14]1[CH2:18][N:17]([C@@H:19]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH3:20])[C:16](=[O:27])[NH:15]1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 11466653HCID 11466653, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 58071963HCID 58071963, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.26 g (R)-2-Oxo-1-((R)-1-phenyl-ethyl)-3-(toluene-4-sulfonyl)-imidazolidine-4-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (I.24) was placed in 20 mL tetrahydrofuran at 0° C. under nitrogen, then 1.12 mL lithium aluminium hydride (2.3M in tetrahydrofuran) was added. The reaction was stirred for 1 h 45 min and then a 10 mL of a saturated solution of sodium sulfate was added. The mixture was extracted with ethyl acetate (×2), dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. Purification by silica gel chromatography (dichloromethane/ethyl acetate 100:0 to 70:30) gave the title compound.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (×2)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customPurification by silica gel chromatography (dichloromethane/ethyl acetate 100:0 to 70:30)

Sources & evidence

ORD record
ord-8811bd93000c4d0f8eb0da5ef9a20ed5
Source dataset
uspto-grants-2015_11
Patent number
US09187478B2

Reaction notes

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