HCID 131724348, compound → HCID 131724347, compound

HRID 2121326Notes

Reaction equation

HRID 2121326 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@@H:2]([C:13]([NH:15][C@H:16]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:17][CH2:18][CH2:19][CH2:20][NH:21]OC(C)(C)C)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1>CO.[Pd]>[NH2:1][C@@H:2]([C:13]([NH:15][C@H:16]([C:27]([O:29][C:30]([CH3:32])([CH3:33])[CH3:31])=[O:28])[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

Participants

4

Reactant 1

HCID 131724348HCID 131724348, compound

Product 1

HCID 131724347HCID 131724347, compoundYield 192.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 590 mg of CBZ-D-Trp-Lys(OtBu)-OtBu was hydrogenated at 50 PSI for 2.5 hours in 50 mL of methanol with 100 mg of 10% palladium on carbon catalyst. The catalyst was then filtered off and the solvent evaporated to yield 466 mg (95%) of D-Trp-Lys(BOC)-OtBu (see Scheme 2A, reactants 9→8).

Workup

  1. filtrationThe catalyst was then filtered off
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-b6dce41e253f4f3fbced8665d4378085
Source dataset
uspto-grants-2004_02
Patent number
US06696418B1

Reaction notes

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