Methanol → HCID 21866635, compound

HRID 857209Notes

Reaction equation

HRID 857209 reaction equation
[C:1]([CH:4]([NH:12][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10])(=[O:3])[CH3:2].S(=O)(=O)(O)O.[CH3:26]O>>[C:1]([CH:4]([NH:12][C:13](=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:26])=[O:10])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 17850954HCID 17850954, compound

Product 1

HCID 21866635HCID 21866635, compound

Procedure

6-Acetyl-6-benzoylaminohexanoic acid (4.35 g) was dissolved in 100 ml of methanol, and 0.5 ml of conc. sulfuric acid was added. The mixture was heated to reflux for 2.5 hours. The reaction solution was cooled, poured into ice-cold water, extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and concentrated to provide 4.4 g of the objective compound as yellowish crystals. M.p. 59-60° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2.5 hours
  3. temperatureThe reaction solution was cooled
  4. additionpoured into ice-cold water
  5. extractionextracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a2b2bc82a51c44f3ab11c784d1d455fc
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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