Isobutyl chloroformate → HCID 13288203, compound

HRID 1903190Notes

Reaction equation

HRID 1903190 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=[O:19])[CH2:13][CH2:12]2)([OH:3])=O.C1CCN2C(=NCCC2)CC1.ClC(OCC(C)C)=O.[OH:39][CH2:40][CH2:41][CH2:42][NH:43][CH2:44][CH:45]1[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1>CO.C(Cl)(Cl)Cl>[CH:45]1([CH2:44][N:43]([CH2:42][CH2:41][CH2:40][OH:39])[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH2:13][CH2:12]3)=[O:3])[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1

Participants

7

Reactant 4

HCID 62365Isobutyl chloroformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 12687390HCID 12687390, compoundHCID 12819307HCID 12819307, compound

Product 1

HCID 13288203HCID 13288203, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent2×

Procedure

Into 400 ml of chloroform, were added 5 g of 6-(4-carboxybutoxy)-3,4-dihydrocarbostyril and 3.2 g of DBU. The outside of the reaction vessel containing the above mentioned mixture was ice-cooled and 2.8 g of isobutyl chloroformate was added dropwise to the mixture under stirring condition. After the addition operation, stirring was continued at a room temperature for 30 minutes and 3.9 g of N-(3-hydroxypropyl)-N-cyclohexylmethylamine was added to the reaction mixture and the reaction was continued for 3 hours. After the reaction was completed, the reaction mixture was washed with 1 N-NaOH aqueous solution, 10% HCl and water in this order and was dried with anhydrous Na2SO4. The drying agent was removed by filtration and the thus obtained dried product was concentrated to obtain a residue. The residue was treated by a silica-gel column chromatography (solvent used was a mixture of chloroform:methanol=40:1). The elute obtained was concentrated and was recrystallized from ethyl acetate-petroleum ether. 4.0 Grams of 6-{4-[N-cyclohexylmethyl-N-(3-hydroxypropyl)aminocarbonyl]butoxy}-3,4-dihydrocarbostyril was obtained in the form of colorless needle-like crystals. Melting point: 95°-97° C.

Workup

  1. additionThe outside of the reaction vessel containing the
  2. temperaturecooled
  3. stirringAfter the addition operation, stirring
  4. waitthe reaction was continued for 3 hours
  5. washthe reaction mixture was washed with 1 N-NaOH aqueous solution, 10% HCl and water in this order
  6. dry with materialwas dried with anhydrous Na2SO4
  7. customThe drying agent was removed by filtration
  8. customthe thus obtained dried product
  9. concentrationwas concentrated
  10. customto obtain a residue
  11. additionThe residue was treated by a silica-gel column chromatography (solvent
  12. customThe elute obtained
  13. concentrationwas concentrated
  14. customwas recrystallized from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-2552c8108baa40938179a0ec6cf9262c
Source dataset
uspto-grants-1984_03
Patent number
US04435404

Reaction notes

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