Methyl 7-chloro-6-oxoheptanoate → HCID 20202828, compound

HRID 543781Notes

Reaction equation

HRID 543781 reaction equation
Cl[CH2:2][C:3](=O)[CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9].[F:13][C:14]([F:24])([F:23])[CH2:15][NH:16][C:17]([NH:19][C:20]([NH2:22])=[S:21])=[NH:18]>CCO>[F:24][C:14]([F:13])([F:23])[CH2:15][N:16]=[C:17]([NH2:18])[NH:19][C:20]1[S:21][CH:2]=[C:3]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])[N:22]=1

Participants

4

Reactant 2

HCID 15576276Methyl 7-chloro-6-oxoheptanoateHCID 178512206HCID 178512206, compound

Product 1

HCID 20202828HCID 20202828, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of methyl 7-chloro-6-oxoheptanoate (2.0 g.) in hot EtOH (20 ml.) was added a solution of 2,2,2-trifluoroethylamidinothiourea (2.1 g.) in hot EtOH (20 ml.). The resulting mixture was heated under reflux for 1 hour. The mixture was then evaporated to dryness and the residue partitioned between ether (20 ml.) and water (60 ml.). The aqueous layer was separated and basified with sodium bicarbonate and extracted with EtOAc. The EtOAc solution was evaporated to dryness and the residue crystallised from EtOAc/ether containing a small amount of acetone to give methyl 5-[2-(2-[2,2,2-trifluoroethyl]guanidino)thiazol-4-yl]valerate which was used without further purification.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customThe mixture was then evaporated to dryness
  4. customthe residue partitioned between ether (20 ml.) and water (60 ml.)
  5. customThe aqueous layer was separated
  6. extractionextracted with EtOAc
  7. customThe EtOAc solution was evaporated to dryness
  8. customthe residue crystallised from EtOAc/ether containing a small amount of acetone

Sources & evidence

ORD record
ord-f4f84448db5c48d2889f6ef096580f2c
Source dataset
uspto-grants-1984_05
Patent number
US04447441

Reaction notes

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