Hydrochloric Acid → HCID 42256687, compound

HRID 1460496Notes

Reaction equation

HRID 1460496 reaction equation
[OH-].[Na+].[NH:3]1[CH2:10][CH2:9][CH2:8][C@H:4]1[C:5]([OH:7])=[O:6].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20](Cl)=[O:21])=[CH:15][CH:14]=1.Cl>O.CC(C)=O>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([N:3]2[CH2:10][CH2:9][CH2:8][C@H:4]2[C:5]([OH:7])=[O:6])=[O:21])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 145742L-ProlineHCID 27346884-Methoxyphenylacetyl chloride

Product 1

HCID 42256687HCID 42256687, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

5M Aqueous sodium hydroxide solution (26 ml) was added to a solution of (S)-proline (582 g) in water (3.5 L) and acetone (3.5 L). The mixture was treated with ice (3.5 kg), cooled in an ice/acetone bath, treated over a one hour period with a solution of 4-methoxyphenylacetyl chloride (944 g) in acetone (1.75 L) with vigorous stirring and the simultaneous addition of sufficient 5M aqueous sodium hydroxide solution in order to keep the pH within the range 9.5-9.7. The reaction was stirred for 30 minutes, treated with concentrated hydrochloric acid (6 ml) and partially evaporated under reduced pressure to remove the majority of the acetone. The residue was treated with ice (2 kg), concentrated hydrochloric acid (750 ml) and the mixture stirred at room temperature for one hour. The resulting precipitate was collected, washed with water and recrystallised from toluene/ethanol to give the desired product as a colourless solid (905 g, 75%), m.p. 138°-139° C.

Workup

  1. temperaturecooled in an ice/acetone bath
  2. stirringThe reaction was stirred for 30 minutes
  3. custompartially evaporated under reduced pressure
  4. customto remove the majority of the acetone
  5. additionThe residue was treated with ice (2 kg), concentrated hydrochloric acid (750 ml)
  6. stirringthe mixture stirred at room temperature for one hour
  7. customThe resulting precipitate was collected
  8. washwashed with water
  9. customrecrystallised from toluene/ethanol

Sources & evidence

ORD record
ord-8af55df730394b93bbd723e6a84cb70d
Source dataset
uspto-grants-1991_12
Patent number
US05071844

Reaction notes

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