Tert-Butylamine → HCID 53746079, compound

HRID 1757761Notes

Reaction equation

HRID 1757761 reaction equation
C(OC(N1[CH2:18][C@H:17]([OH:19])[CH2:16][C@H:12]1[C:13]([OH:15])=O)=O)C1C=CC=CC=1.C([N:22]1CCOCC1)C.Cl[C:29]([O:31][CH2:32][CH:33]([CH3:35])[CH3:34])=[O:30].[C:36]([NH2:40])([CH3:39])([CH3:38])[CH3:37].O1C[CH2:44][CH2:43][CH2:42]1>C(OCC)C>[CH2:32]([O:31][C:29]([NH:22][C:13](=[O:15])[C@@H:12]1[CH2:16][C@@H:17]([OH:19])[CH2:18][N:40]1[C:36]([CH3:39])([CH3:38])[CH3:37])=[O:30])[C:33]1[CH:35]=[CH:44][CH:43]=[CH:42][CH:34]=1

Participants

7

Reactant 5

HCID 6385Tert-ButylamineHCID 7525EthylmorpholineHCID 8028TetrahydrofuranHCID 62365Isobutyl chloroformateHCID 3915171-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Product 1

HCID 53746079HCID 53746079, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-10 °C

Procedure

2.65 g of N-(benzyloxycarbonyl)-4(R)-hydroxy-L-proline were dissolved in 10 ml of dry tetrahydrofuran and cooled to -10° C. while stirring with a magnetic stirrer. 1.15 g of N-ethylmorpholine were added followed immediately by 1.36 g of isobutyl chloroformate. The mixture was stirred at -10° C. for 30 minutes and then 2.19 g of tert.butylamine were added. Stirring was continued at -10° C. for 1hour, the mixture was allowed to warm to room temperature during 2 hours and was then left to stand for 2 hours. The solvent was removed by evaporation in a vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was washed with 10% citric acid solution and sodium bicarbonate solution and then dried over sodium sulphate. The solvent was removed by evaporation to give a solid which wastriturated with diethyl ether and filtered off. There were obtained 2.23 g of crude product which was recrystallized from ethyl acetate/diethyl etherto give 1.57 g of N2 (benzyloxycarbonyl)-N1 -tert butyl-4(R)-hydroxy-L-prolinamide of melting point 128°-130° C.

Workup

  1. stirringThe mixture was stirred at -10° C. for 30 minutes
  2. stirringStirring
  3. temperatureto warm to room temperature during 2 hours
  4. waitwas then left
  5. waitto stand for 2 hours
  6. customThe solvent was removed by evaporation in a vacuum
  7. customthe residue was partitioned between ethyl acetate and water
  8. washThe organic layer was washed with 10% citric acid solution and sodium bicarbonate solution
  9. dry with materialdried over sodium sulphate
  10. customThe solvent was removed by evaporation
  11. customto give a solid which
  12. filtrationfiltered off
  13. customThere were obtained 2.23 g of crude product which
  14. customwas recrystallized from ethyl acetate/diethyl

Sources & evidence

ORD record
ord-54b04526fe33457e964fb6c34e43e057
Source dataset
uspto-grants-1995_08
Patent number
US05446161

Reaction notes

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