HCID 20253232, compound → HCID 20253230, compound

HRID 638098Notes

Reaction equation

HRID 638098 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([CH2:12][CH3:13])[CH:9]2[C:14]([OH:16])=[O:15])C=CC=CC=1.[H][H]>[Pd].C(O)C>[CH2:12]([CH:10]1[CH2:11][NH:8][CH:9]1[C:14]([OH:16])=[O:15])[CH3:13]

Participants

5

Reactant 2

HCID 20253232HCID 20253232, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20253230HCID 20253230, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

8 g of 2B, 100 ml of ethanol and 70 g of 5% palladium charcoal catalyst was hydrogenated at ambient temperature at a hydrogen pressure of between 3 and 4 atomospheres absolute for 10 hours in a Parr apparatus. The resulting mixture was filtered, evaporated to dryness and partitioned between methylene chloride and water. The aqueous phase was separated, evaporated to a low bulk and poured onto a Dowex 8-50 x(H) resin column. Isolation of the imino acid was achieved by eluting the washed column with a 2M ammonia solution. Evaporation of the washings left a white solid which on recrystallization from ethanol deposited an isomer mixture [1α:3β] of 2. Evaporation of the recrystallizing medium left additional 2, having a different isomer composition [2α:3β].

Workup

  1. filtrationThe resulting mixture was filtered
  2. customevaporated to dryness
  3. custompartitioned between methylene chloride and water
  4. customThe aqueous phase was separated
  5. customevaporated to a low bulk
  6. additionpoured onto a Dowex 8-50 x(H) resin column
  7. washby eluting the washed column with a 2M ammonia solution
  8. customEvaporation of the washings
  9. waitleft a white solid which
  10. customon recrystallization from ethanol
  11. customEvaporation of the recrystallizing medium
  12. waitleft additional 2

Sources & evidence

ORD record
ord-f75f87cf5634415092dba5db3e582a8b
Source dataset
uspto-grants-1985_12
Patent number
US04560401

Reaction notes

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