HCID 14819147, compound → HCID 14819161, compound

HRID 2352397Notes

Reaction equation

HRID 2352397 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]([CH3:30])[NH:17][CH:18]1[CH2:22][CH:21]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[O:20][C:19]1=[O:29])C1C=CC=CC=1>CO.[Pd]>[O:29]=[C:19]1[CH:18]([NH:17][C@H:16]([C:15]([N:11]2[CH2:12][CH2:13][CH2:14][C@H:10]2[C:9]([OH:32])=[O:8])=[O:31])[CH3:30])[CH2:22][CH:21]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[O:20]1

Participants

4

Reactant 1

HCID 14819147HCID 14819147, compound2×

Product 1

HCID 14819161HCID 14819161, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dissolved in 50 ml of methanol was 3.80 g of Isomer B of N-(2-oxo-5-hexyl-3-tetrahydrofuranyl)-L-alanyl-L-proline benzyl ester (Compound 7). Thereafter, 0.40 g of 10% palladium-charcoal was added and the reaction mixture was hydrogenated at room temperature and normal pressure for 2 hours. The palladium-charcoal was then filtered off and the filtrate was distilled under reduced pressure to obtain as white powder 2.80 g of N-(2-oxo-5-hexyl-3-tetrahydrofuranyl)-L-alanyl-L-proline (Isomer B) [in the formula (I), R1 =--(CH2)5CH3, R2 =H, R3 =CH3, R4 and R5 =--(CH2)3 --, R6 =H (Compound 14)].

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe palladium-charcoal was then filtered off
  3. distillationthe filtrate was distilled under reduced pressure

Sources & evidence

ORD record
ord-84a0759b76bd4cf78223d9ab8472ef5c
Source dataset
uspto-grants-1989_10
Patent number
US04876359

Reaction notes

Loading…