HCID 178418361, compound → HCID 178427506, compound

HRID 1417898Notes

Reaction equation

HRID 1417898 reaction equation
[NH:1]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[C@@H:2]([C:6]([N:8]([CH3:41])[C@H:9]([C:27]([NH:29][CH2:30][C:31]([O:33]CC1C=CC=CC=1)=[O:32])=[O:28])[CH2:10][CH2:11][CH2:12][NH:13][C:14](=[NH:26])[NH:15][S:16]([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17])=[O:7])[CH:3]([CH3:5])[CH3:4].[H][H]>CO.[Pd]>[NH:1]([C:42]([O:44][C:45]([CH3:47])([CH3:46])[CH3:48])=[O:43])[C@@H:2]([C:6]([N:8]([CH3:41])[C@H:9]([C:27]([NH:29][CH2:30][C:31]([OH:33])=[O:32])=[O:28])[CH2:10][CH2:11][CH2:12][NH:13][C:14](=[NH:26])[NH:15][S:16]([C:19]1[CH:20]=[CH:21][C:22]([CH3:23])=[CH:24][CH:25]=1)(=[O:18])=[O:17])=[O:7])[CH:3]([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178427503HCID 178427503, compound

Product 1

HCID 178427506HCID 178427506, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of Boc-D-Val-NMeArg(Tos)-Gly-OBzl (4.50 g, 6.53 mmol) in 80 ml of methanol was purged with nitrogen gas, 1.30 g of 10% Pd/C was added, and hydrogen gas was passed over the reaction. After 1 hour the catalyst was removed by filtration through a bed of celite, and the solvent removed under reduced pressure. The resulting solid was triturated with ether, filtered, and washed with petroleum ether to provide Boc-D-Val-NMeArg(Tos)-Gly (3.05 g, 78%); 1H NMR (D6 -DMSO) d 7.90 (br t, 1H), 7.65 (d, 2H), 7.30 (d, 2H), 7.00 (d, 1H), 6.85 (br d, 1H), 6.60 (br s, 1H), 5.00 (dd, 1H), 4.15 (t, 1H), 3.70 (m, 2H), 3.05 (m, 2H), 2.90 (s, 3H), 2.35 (s, 3H), 1.90 (m, 2H), 1.55 (m, 1H), 1.35 (s, 9H), 1.25 (m, 2H), 0.80 (br t, 6H); FAB-MS: [M+H]=599.45.

Workup

  1. additionwas added
  2. customAfter 1 hour the catalyst was removed by filtration through a bed of celite
  3. customthe solvent removed under reduced pressure
  4. customThe resulting solid was triturated with ether
  5. filtrationfiltered
  6. washwashed with petroleum ether

Sources & evidence

ORD record
ord-bbf9872a37344b1bb0d2bb198d4a3fe0
Source dataset
uspto-grants-1999_03
Patent number
US05879657

Reaction notes

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