HCID 53822454, compound → HCID 54378965, compound

HRID 2413728Notes

Reaction equation

HRID 2413728 reaction equation
C([O:8][C:9](=[O:32])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:31])[C@@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[C:21](=[O:30])[C@H:22]([CH3:29])[NH:23][S:24]([CH2:27][CH3:28])(=[O:26])=[O:25])C1C=CC=CC=1.[H][H]>CO.O.[C].[Pd]>[CH2:27]([S:24]([NH:23][C@H:22]([C:21]([N:17]1[CH2:18][CH2:19][CH2:20][C@H:16]1[C:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[C:9]([OH:32])=[O:8])=[O:31])=[O:30])[CH3:29])(=[O:25])=[O:26])[CH3:28]

Participants

6

Reactant 2

HCID 53822454HCID 53822454, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54378965HCID 54378965, compoundYield 72.5%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-ethanesulfonyl-L-alanyl-L-prolyl-L-proline benzylester (2.00 g, 4.29 m mole) was dissolved in a mixture of methanol (10 ml) and water (10 ml), and then hydrogen gas was passed through the solution in the presence of 5% palladium carbon for 1.5 hours at room temperature. Cellite was added to the reaction solution and the solution was filtered and this operation was repeated again. The catalyst was completely removed and the filtrate was concentrated under reduced pressure. The thus produced crystals were obtained by filtration, washed sufficiently with ethyl acetate, and then dried under reduced pressure to give white crystals of N-ethanesulfonyl-L-alanyl-L-prolyl-L-proline (1.17 g).

Workup

  1. additionCellite was added to the reaction solution
  2. filtrationthe solution was filtered
  3. customThe catalyst was completely removed
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe thus produced crystals were obtained by filtration
  6. washwashed sufficiently with ethyl acetate
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-c623dfa15d0f482093f30515e20c78d7
Source dataset
uspto-grants-1988_01
Patent number
US04719200

Reaction notes

Loading…