Water → HCID 13501958, compound

HRID 462866Notes

Reaction equation

HRID 462866 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:7]([NH:9][C@H:10]([C:23]([OH:25])=[O:24])[CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].O>CO.[Pd]>[NH2:1][C@H:2]([C:7]([NH:9][C@H:10]([C:23]([OH:25])=[O:24])[CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 962WaterHCID 13501956Z-Leu-Lys(Boc)-OH

Product 1

HCID 13501958HCID 13501958, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of Z-Leu-Lys(Boc)-OH 41.5 g, 0.084 mol) in methanol (210 mL) was hydrogenated in a Vibromixer apparatus using 10% Pd/C (5.0 g) for 3.5 h. The precipitated product dissolved on addition of H2O (120 mL). The catalyst was removed by filtration (celite); washed twice with H2O and the combined filtrate evaporated to near dryness. The residue was reevaporated from MeOH (2×) and Et2O (2×). The solid product was collected, washed with Et2O and dried to afford 26.9 g of white solid. Recrystallization from warm iPrOH (420 ml) and MeOH (350 mL) afforded, after drying, 24.6 g of white crystalline product (81.5%); mp 142°-143°; Rf 0.63 (n-BuOH:AcOH:EtOAc:H2O; 1-1-1-1); [α]D25 +20.76° (c 1, MeOH). Anal: calcd. for C17H33N3O5 (359.47): C, 56.80; H, 9.25; N, 11.69. Found: C, 56.72; H, 9.55; N, 11.57.

Workup

  1. customfor 3.5 h
  2. customThe catalyst was removed by filtration (celite)
  3. washwashed twice with H2O
  4. customthe combined filtrate evaporated
  5. customThe residue was reevaporated from MeOH (2×) and Et2O (2×)
  6. customThe solid product was collected
  7. washwashed with Et2O
  8. customdried

Sources & evidence

ORD record
ord-ffa3b23b95e244a98c061cd0d870f658
Source dataset
uspto-grants-1985_05
Patent number
US04517119

Reaction notes

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