Lithium Chloride → HCID 22279870, compound

HRID 2086180Notes

Reaction equation

HRID 2086180 reaction equation
C([O:3][C:4](=O)[C:5]([NH:14][C:15]([O:17][CH3:18])=[O:16])([CH3:13])[CH2:6][CH2:7][C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)C.[BH4-].[Na+].[Cl-].[Li+]>C(O)C.O1CCCC1>[CH3:18][O:17][C:15]([NH:14][C:5]([CH3:13])([CH2:6][CH2:7][C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)[CH2:4][OH:3])=[O:16]

Participants

6

Reactant 3

HCID 433294Lithium Chloride2×HCID 4311764Sodium borohydride2×HCID 69338213HCID 69338213, compound

Product 1

HCID 22279870HCID 22279870, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Methoxycarbonylamino-2-methyl-4-(2-thienyl)butanoic acid ethylester (14.7 g, 51.6 mmol) obtained in Example 1(c) was dissolved in a mixture of ethanol (150 ml) and tetrahydrofuran (100 ml), and then sodium borohydride (5.07 g, 0.13 mol) and lithium chloride (5.68 g, 0.13 mol) were added thereto followed by stirring overnight at room temperature under a nitrogen atmosphere. And next morning, sodium borohydride (5.07 g, 0.13 mol) and lithium chloride (5.68 g, 0.13 mol) were added thereto in a similar way, and the reaction mixture was stirred once more overnight at room temperature under a nitrogen atmosphere. Similar procedures described above were carried out for more two days. The reaction mixture was poured into ice-cold 10% hydrochloric acid (500 ml), and the resulting solution was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was concentrated in vacuo, and the residue was purified by flash chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=2:1-1:5) to afford the title compound (11.7 g, 93% yield) as a white crystalline solid.

Workup

  1. stirringin a similar way, and the reaction mixture was stirred once more overnight at room temperature under a nitrogen atmosphere
  2. waitabove were carried out for more two days
  3. extractionthe resulting solution was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe solvent was concentrated in vacuo
  7. customthe residue was purified by flash chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=2:1-1:5)

Sources & evidence

ORD record
ord-c29df13c16dd4743ac98f4c40da742ce
Source dataset
uspto-grants-2004_04
Patent number
US06723745B2

Reaction notes

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