Potassium ethanethioate → HCID 53832870, compound

HRID 849551Notes

Reaction equation

HRID 849551 reaction equation
CS([O:5][CH:6]([C:26]([NH:28][CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1)=[O:27])[CH2:7][CH2:8][S:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:14]=1)(=[O:11])=[O:10])(=O)=O.[C:37]([O-])(=[S:39])[CH3:38].[K+]>CN(C=O)C>[C:37](=[S:39])([O:5][CH:6]([C:26]([NH:28][CH2:29][CH2:30][N:31]1[CH2:32][CH2:33][O:34][CH2:35][CH2:36]1)=[O:27])[CH2:7][CH2:8][S:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:14]=1)(=[O:10])=[O:11])[CH3:38]

Participants

4

Reactant 2

HCID 23670855Potassium ethanethioateHCID 86755042HCID 86755042, compound

Product 1

HCID 53832870HCID 53832870, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Part I: A solution of 2.5 g (5 mmol) of 1-[(2-morpholinoethyl)amino]carbonyl-3-[(3-phenoxybenzyl)sulfonyl]propyl methanesulfonate from Part H in 20 mL of anhydrous DMF was treated with 0.8 g (7 mM) of potassium thioacetate. After 1 hour, the reaction was partitioned between ethyl acetate and sodium bicarbonate solution. The layers were separated and the organic layer was washed with brine (3×), dried (MgSo4) and concentrated to yield 2.4 g of crude product. This was chromatographed on silica gel using 1-3% methanol/ethyl acetate to yield 1.8 g of 1-[(2-morpholinoethyl)amino]carbonyl-3-[(3-phenoxybenzyl)sulfonyl]propyl ethanethioate suitable for the next reaction.

Workup

  1. customthe reaction was partitioned between ethyl acetate and sodium bicarbonate solution
  2. customThe layers were separated
  3. washthe organic layer was washed with brine (3×)
  4. customdried (MgSo4)
  5. concentrationconcentrated
  6. customto yield 2.4 g of crude product
  7. customThis was chromatographed on silica gel using 1-3% methanol/ethyl acetate

Sources & evidence

ORD record
ord-01e62c35fac24c2b82c718a2ae501ee4
Source dataset
uspto-grants-2000_01
Patent number
US06013649

Reaction notes

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