Lithium Chloride → HCID 67206860, compound

HRID 1013428Notes

Reaction equation

HRID 1013428 reaction equation
[Cl-].[Li+].C([O:5][C:6]([C:8]1[C:19]2[CH:18]3[CH:14]([CH2:15][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17]3)[CH2:13][CH2:12][C:11]=2[S:10][CH:9]=1)=O)C.[BH4-].[Li+]>C1COCC1>[C:23]([O:22][C:20]([N:16]1[CH2:15][CH:14]2[CH:18]([C:19]3[C:8]([CH2:6][OH:5])=[CH:9][S:10][C:11]=3[CH2:12][CH2:13]2)[CH2:17]1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 433294Lithium ChlorideHCID 4148881Lithium borohydrideHCID 58624929HCID 58624929, compound

Product 1

HCID 67206860HCID 67206860, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Lithium chloride (2.77 g, 0.066 mol) was added to the product of step e) (5.8 g, 0.016 mol) in 200 mL of THF followed by the addition of 2.0 M lithium borohydride (58 mL, 0.115 mol). The reaction was stirred overnight at 60° C. and was then cooled to room temperature. The reaction mixture was filtered through Celite, diluted with 100 mL of water and was extracted with ethyl acetate (3×150 mL). The combined ethyl acetate extracts were dried (MgSO4) and the solvent evaporated in vacuo to give the subtitle compound that was used without further purification. MS calculated for C16H23NO3S +H: 310, observed: 310.

Workup

  1. temperaturewas then cooled to room temperature
  2. filtrationThe reaction mixture was filtered through Celite
  3. additiondiluted with 100 mL of water
  4. extractionwas extracted with ethyl acetate (3×150 mL)
  5. dry with materialThe combined ethyl acetate extracts were dried (MgSO4)
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-9801ef69f1b34e90969aaef8e97a69e3
Source dataset
uspto-grants-2011_07
Patent number
US07981919B2

Reaction notes

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