Hydrochloric Acid → HCID 54175967, compound

HRID 903451Notes

Reaction equation

HRID 903451 reaction equation
C[O:2][C:3](=[O:23])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9](=[O:22])[CH:10]([CH3:21])[CH2:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1.[OH-].[Na+].Cl>O1CCCC1>[F:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[C:12]([CH2:11][CH:10]([CH3:21])[C:9]([N:5]1[CH2:6][CH2:7][CH2:8][C@H:4]1[C:3]([OH:23])=[O:2])=[O:22])=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54270278HCID 54270278, compound

Product 1

HCID 54175967HCID 54175967, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1.98 g. portion of 1-[3-(3-fluorobenzoyl)-2-methylpropionyl]-L-proline methyl ester (Example 44) is dissolved in 2 ml. of tetrahydrofuran and 20 ml. of 1 N sodium hydroxide is added. The mixture is stirred at room temperature for 4 hours, cooled in an ice bath, acidified with concentrated hydrochloric acid and extracted with dichloromethane. The organic extract is washed with sodium chloride solution, dried over magnesium sulfate and evaporated in vacuo to a gum. This gum is triturated with ether giving the desired product as 500 mg. of a white solid.

Workup

  1. temperaturecooled in an ice bath
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. washis washed with sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo to a gum
  7. customThis gum is triturated with ether giving the desired product as 500 mg

Sources & evidence

ORD record
ord-27a06b1050e840039e0a895114bdf877
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

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