Sodium sulfate decahydrate → HCID 86666310, compound

HRID 1026325Notes

Reaction equation

HRID 1026325 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:22])[CH2:10][O:11][C:12]1[CH:21]=[CH:20][C:15]([C:16](OC)=[O:17])=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].OCC1C=CC(OC[C@@H](NC(=O)OC(C)(C)C)C)=CC=1>C1COCC1.O.C(N(CC)CC)C.CS(C)=O.C1(C)C=CC=CC=1>[CH:16]([C:15]1[CH:14]=[CH:13][C:12]([O:11][CH2:10][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH3:22])=[CH:21][CH:20]=1)=[O:17]

Participants

10

Reactant 4

HCID 62649Sodium sulfate decahydrateHCID 21225700DiisobutylaluminumhydrideHCID 67777192HCID 67777192, compound3×HCID 86666311HCID 86666311, compound2×

Product 1

HCID 86666310HCID 86666310, compoundYield 68.4%

Reagents, catalysts & solvents 5

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of methyl 4-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)benzoate (816 mg) in THF (10 mL) was added a toluene solution (1.0 M, 5.28 mL) of diisobutylaluminum hydride at −78° C., and the mixture was stirred at room temperature for 30 min under an argon atmosphere. Sodium sulfate decahydrate (22.7 g) was added thereto at −78° C., and the mixture was stirred at room temperature for 3 hr. The reaction mixture was filtered through celite, and the solvent of the filtrate was evaporated under reduced pressure to give a mixture of tert-butyl {(1S)-2-[4-(hydroxymethyl)phenoxy]-1-methylethyl}carbamate and methyl 4-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)benzoate as a pale-yellow oil (813 mg). A mixture of the aforementioned mixture (813 mg) of tert-butyl {(1S)-2-[4-(hydroxymethyl)phenoxy]-1-methylethyl}carbamate and methyl 4-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)benzoate, sulfur trioxide pyridine complex (657 mg), DMSO (7 mL) and triethylamine (3 mL) was stirred at room temperature for 2 hr. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The combined organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a colorless oil (504 mg).

Workup

  1. stirringat −78° C., and the mixture was stirred at room temperature for 3 hr
  2. filtrationThe reaction mixture was filtered through celite
  3. customthe solvent of the filtrate was evaporated under reduced pressure
  4. customto give
  5. stirringwas stirred at room temperature for 2 hr
  6. extractionthe mixture was extracted twice with ethyl acetate
  7. washThe combined organic layer was washed with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-92b441ba569e468583c6904ace5ce1b5
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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