HCID 131724673, compound → HCID 131724672, compound

HRID 2417162Notes

Reaction equation

HRID 2417162 reaction equation
[NH:1]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C@@H:2]([C:10]([NH:12][C@H:13]([C:18]([N:20]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:21]1[C:22]([O:24]CC1C=CC=CC=1)=[O:23])=[O:19])[C@H:14]([CH2:16][CH3:17])[CH3:15])=[O:11])[CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1>CO.[Pd]>[NH:1]([C:36]([O:38][C:39]([CH3:41])([CH3:40])[CH3:42])=[O:37])[C@@H:2]([C:10]([NH:12][C@H:13]([C:18]([N:20]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:21]1[C:22]([OH:24])=[O:23])=[O:19])[C@H:14]([CH2:16][CH3:17])[CH3:15])=[O:11])[CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 1

HCID 131724673HCID 131724673, compound

Product 1

HCID 131724672HCID 131724672, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Boc-D-Cha-L-Ile-D,L-Pip-OBzl (565 mg, 0.96 mmol) was dissolved in MeOH (10 ml). Pd-C catalyst (250 mg) was added to the solution and the solution was stirred for 15 hours under hydrogen atmosphere to remove the benzyl ester group. After Pd-C catalyst was filtered off, MeOH was distilled off to give a residue, which was then vacuum dried to yield Boc-D-Cha-L-Ile-D,L-Pip-OH (459 mg, 0.93 mmol; yield 97%) as a foam.

Workup

  1. customto remove the benzyl ester group
  2. filtrationAfter Pd-C catalyst was filtered off
  3. distillationMeOH was distilled off
  4. customto give a residue, which
  5. customvacuum dried

Sources & evidence

ORD record
ord-f563585ae6e74c0a808704182a5ab3bb
Source dataset
uspto-grants-2004_11
Patent number
US06825317B2

Reaction notes

Loading…