Water → HCID 21866700, compound

HRID 890661Notes

Reaction equation

HRID 890661 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([NH:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)=[O:12])[C:7]([OH:9])=O.[C:20](OC(=O)CC)(=O)[CH2:21]C.O>N1C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([NH:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)=[O:12])[C:7](=[O:9])[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 31263Propionic anhydrideHCID 21866926HCID 21866926, compound

Product 1

HCID 21866700HCID 21866700, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

6-Chloro-2-(p-toluoylamino)hexanoic acid (10.0 g) was dissolved in 15 ml of dry pyridine, and 15 ml of propionic anhydride was added and stirred for 2.5 hours at 90° C. To the mixture was added 15 ml of water slowly so that the maximum temperature did not exceed 85° C., and stirred for 20 minutes at 80° C. The reaction solution was cooled, poured into ice-cold water and extracted with diethyl ether. The extract was washed with 10% hydrochloric acid, an aqueous solution of saturated sodium hydrogen carbonate and brine sequentially, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=8:1–4:1) to provide 6.0 g of the objective compound as colorless crystals. M.p. 85–86° C.

Workup

  1. customdid not exceed 85° C.
  2. stirringstirred for 20 minutes at 80° C
  3. temperatureThe reaction solution was cooled
  4. additionpoured into ice-cold water
  5. extractionextracted with diethyl ether
  6. washThe extract was washed with 10% hydrochloric acid
  7. dry with materialan aqueous solution of saturated sodium hydrogen carbonate and brine sequentially, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=8:1–4:1)

Sources & evidence

ORD record
ord-be072dc9c754443c9592ab929f876b47
Source dataset
uspto-grants-2006_02
Patent number
US06998412B2

Reaction notes

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