Sulfuric Acid → HCID 22865735, compound

HRID 744783Notes

Reaction equation

HRID 744783 reaction equation
C(S)C1C=CC=CC=1.C([Li])CCC.[CH:14]([C@@H:17]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]([CH3:43])([CH3:42])[CH3:41])=[C:36]([O:44]C(=O)C)[CH:35]=1)[C:18](N1[C@H](CC2C=CC=CC=2)COC1=O)=[O:19])([CH3:16])[CH3:15].[H-].[H-].[H-].[H-].[Li+].[Al+3].OS(O)(=O)=O>O1CCCC1.CCCCCC.O1CCCC1.O.C(OCC)(=O)C>[CH:14]([C@@H:17]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]([CH3:41])([CH3:43])[CH3:42])=[C:36]([OH:44])[CH:35]=1)[CH2:18][OH:19])([CH3:16])[CH3:15]

Participants

10

Reactant 5

HCID 1118Sulfuric AcidHCID 7509Benzyl mercaptanHCID 21226445Aluminium lithium hydrideHCID 53647758HCID 53647758, compoundHCID 178418339Butyllithium

Product 1

HCID 22865735HCID 22865735, compound

Reagents, catalysts & solvents 4

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

To a solution, stirred at 0° C., of 12.3 ml of benzyl mercaptan in 100 ml of tetrahydrofuran there are added dropwise 49 ml of a 1.6M solution of butyllithium in hexane and after a further 15 minutes' stirring at 0° C. a solution of 12.1 g of 3-[2(R)-isopropyl-3-(3-acetoxy-4-tert-butyl-phenyl)-propanoyl]-4(R)-benzyl-oxazolidin-2-one in 100 ml of tetrahydrofuran. The reaction solution is stirred at 0° C. for a further 90 minutes and is then added dropwise at 0° C., with stirring, to a suspension of 4.9 g of LiAlH4 in 100 ml of tetrahydrofuran. The reaction mixture is stirred for a further 150 minutes at 0° C. and then, in succession, 26.8 ml of ethyl acetate, 100 ml of tetrahydrofuran/water=1:1 and 400 ml of 2N H2SO4 are added dropwise thereto. The tetrahydrofuran is removed using a rotary evaporator and the suspension that remains is partitioned between diethyl ether and water. The organic phases are concentrated by evaporation and the residue is purified by FC (300 g of silica gel, dichloromethane/ethyl acetate=9:1 and 200 g of silica gel, ethyl acetate/hexane=1:2), yielding the title compound: Rf (ethyl acetate/hexane=1:2)=0.43.

Workup

  1. additionis then added dropwise at 0° C.
  2. stirringThe reaction mixture is stirred for a further 150 minutes at 0° C.
  3. customThe tetrahydrofuran is removed
  4. customa rotary evaporator
  5. customthe suspension that remains is partitioned between diethyl ether and water
  6. concentrationThe organic phases are concentrated by evaporation
  7. customthe residue is purified by FC (300 g of silica gel, dichloromethane/ethyl acetate=9:1 and 200 g of silica gel, ethyl acetate/hexane=1:2)

Sources & evidence

ORD record
ord-9165cd3d1c0f4741aba38034cbf40580
Source dataset
uspto-grants-1996_09
Patent number
US05559111

Reaction notes

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