Tetrahydrofuran → HCID 86635704, compound

HRID 1716471Notes

Reaction equation

HRID 1716471 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C@@H:8]([CH2:16][C:17]1[CH:25]=[C:24]([Cl:26])[C:20]2[O:21][CH2:22][O:23][C:19]=2[CH:18]=1)[C:9](=[O:15])[C:10]1[S:11][CH:12]=[CH:13][N:14]=1)([CH3:4])([CH3:3])[CH3:2].[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].C1COCC1>CCO>[Cl:26][C:24]1[C:20]2[O:21][CH2:22][O:23][C:19]=2[CH:18]=[C:17]([CH2:16][C@H:8]([NH:7][C:6](=[O:27])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[C@H:9]([OH:15])[C:10]2[S:11][CH:12]=[CH:13][N:14]=2)[CH:25]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 67165422HCID 67165422, compound

Product 1

HCID 86635704HCID 86635704, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A cooled solution (0° C.) of (S)-tert-butyl3-(7-chlorobenzo[d][1,3]dioxol-5-yl)-1-oxo-1-(thiazol-2-yl)propan-2-ylcarbamate (4.220 g, 10 mmol) in EtOH (60 mL) was added dropwise via cannula to a cooled solution (−78° C.) of lithium tri-tert-butoxyaluminum hydride 1M in THF (21 ml, 21 mmol) in EtOH (40 mL). After stirring for 2 hours, the reaction mixture was quenched with 1N HCl and diluted with EtOAc. The organic layer was washed with water, saturated NaHCO3 solution, and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The crude residue was crystalized from hot EtOH/water and the solid was collected yielding tert-butyl(1S,2S)-3-(7-chlorobenzo[d][1,3]dioxol-5-yl)-1-hydroxy-1-(thiazol-2-yl)propan-2-ylcarbamate (3.250 g, 77% yield) as a white solid.

Workup

  1. customthe reaction mixture was quenched with 1N HCl
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with water, saturated NaHCO3 solution, and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was crystalized from hot EtOH/water
  7. customthe solid was collected

Sources & evidence

ORD record
ord-b7a30b1d0d6e493aaaa3410f24f7708d
Source dataset
uspto-grants-2010_09
Patent number
US07803809B2

Reaction notes

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