4-Toluenesulfonyl chloride → HCID 86761068, compound

HRID 2245390Notes

Reaction equation

HRID 2245390 reaction equation
[OH:1][CH:2]([CH2:10][CH3:11])[C:3]([O:5][CH2:6][CH:7]([CH3:9])[CH3:8])=[O:4].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.C1N2CCN(CC2)C1.C(N(CC)CC)C>C(OCC)(=O)C.C(#N)C>[S:18]([O:1][CH:2]([CH2:10][CH3:11])[C:3]([O:5][CH2:6][CH:7]([CH3:8])[CH3:9])=[O:4])([C:15]1[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=1)(=[O:20])=[O:19]

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 9237DabcoHCID 21572595HCID 21572595, compound

Product 1

HCID 86761068HCID 86761068, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent3×

Procedure

To a solution of (S) isobutyl 2-hydroxybutyrate (2.72 Kg) and p-toluenesulfonylchloride (3.6 Kg) in ethyl acetate (14 L) at 20° C. was added a solution of DABCO (286 g) and triethylamine (4.7 L) in ethyl acetate (10 L) over 2 h. The reaction was aged at 20-25° C. for 4 h. The mixture was washed with three times with water (10 L, 2 L and 2 L) and the organics concentrated and solvent switched into toluene. The concentrated toluene solution of (S) 2-isobutyl tosylbutyrate was used as is in coupling reaction. Alternatively, acetonitrile can be used in place of ethyl acetate, in which case the reaction proceeds faster.

Workup

  1. washThe mixture was washed with three times with water (10 L, 2 L and 2 L)
  2. concentrationthe organics concentrated
  3. customreaction

Sources & evidence

ORD record
ord-8acb0412f17b4cce88dbf41ab2464256
Source dataset
uspto-grants-2010_03
Patent number
US07683092B2

Reaction notes

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