Methanol → HCID 19593934, compound

HRID 612323Notes

Reaction equation

HRID 612323 reaction equation
[C:1]([S:4][CH2:5][CH2:6][C:7](=[O:15])[NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:14])[CH3:13])(=O)[CH3:2].ClCC[S:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1.[OH-].[K+].CO>O>[C:12]([NH:11][CH2:10][CH2:9][NH:8][C:7](=[O:15])[CH2:6][CH2:5][S:4][CH2:1][CH2:2][S:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1)(=[O:14])[CH3:13]

Participants

6

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 19593895HCID 19593895, compoundHCID 86754362HCID 86754362, compound

Product 1

HCID 19593934HCID 19593934, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A quantity of the S-{2-[N-(2-acetylaminoethyl)carbamoyl]ethyl} thioacetate, prepared above, (3.2 g, 23 mmol), 2-(2-chloroethylthio)tetrahydropyran (2 g, 11 mmol), potassium hydroxide (2.5 g, 44 mmol), methanol (10 cm3) and water (5 cm3) were mixed together and heated at 75° C. for 30 min. The mixture was allowed to cool and then partitioned between chloroform (50 cm3) and water (50 cm3). The organic layer was separated and the aqueous layer extracted with a further portion of chloroform. The combined chloroform extracts were then dried (MgSO4) and volatile components removed under reduced pressure to leave the crude product as an oily solid. A quantity of this material was purified firstly by chromatography on silica using a mixture of ethyl acetate, and methanol (95:5) as the eluant and then by reverse phase h.p.l.c. using aqueous methanol as the eluant. The pure N-(2-acetylaminoethyl)-3-[2-(tetrahydropyran-2-ylthio)ethylthi o]propionamide was obtained as a white solid (0.3 g).

Workup

  1. additionwere mixed together
  2. temperatureto cool
  3. custompartitioned between chloroform (50 cm3) and water (50 cm3)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer extracted with a further portion of chloroform
  6. dry with materialThe combined chloroform extracts were then dried (MgSO4) and volatile components
  7. customremoved under reduced pressure
  8. customto leave the crude product as an oily solid
  9. customA quantity of this material was purified firstly by chromatography on silica using
  10. additiona mixture of ethyl acetate, and methanol (95:5) as the eluant

Sources & evidence

ORD record
ord-be53340275cc417cbd147afb1da78600
Source dataset
uspto-grants-1999_12
Patent number
US06004531

Reaction notes

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