Water → Nepsilon-tert.butoxycarbonyl-L-lysyl-L-proline isobutylamide

HRID 1731972

Reaction equation

HRID 1731972 reaction equation
[CH2:1]([NH:5][C:6](=[O:38])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:37])[C@H:13]([CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[NH:14]C(OCC1C=CC=CC=1)=O)[CH:2]([CH3:4])[CH3:3].C12(CC=O)CC3CC(CC(C3)C1)C2.O.C(=O)(O)[O-].[K+].ClC(OCC1C=CC=CC=1)=O>CO.C(OCC)C.[Pd].CCCCCC.C(OCC)(=O)C>[CH2:1]([NH:5][C:6](=[O:38])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:37])[C@H:13]([CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[NH2:14])[CH:2]([CH3:4])[CH3:3]

Participants

10

Reactant 5

HCID 962WaterHCID 10387Benzyl chloroformateHCID 516893Potassium BicarbonateHCID 50860842-(Adamantan-1-yl)acetaldehydeHCID 131714979Nalpha-benzyloxycarbonyl-Nepsilon-tert.butoxycarbonyl-L-lysyl-L-proline isobutylamide

Product 1

HCID 131714978Nepsilon-tert.butoxycarbonyl-L-lysyl-L-proline isobutylamide

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A solution of 6.3 g (0.012 mol) of Nα -benzyloxycarbonyl-Nε -tert.butoxycarbonyl-L-lysyl-L-proline isobutylamide in 100 ml of methanol was hydrogenated for 3 hours in the presence of 0.6 g of 5% palladium/carbon. A solution of 2.2 g (0.012 mol) of adamantane acetaldehyde in 5 ml of methanol was added via a septum cap and the hydrogenation was continued for 16 hours. The catalyst was removed by filtration and the filtrate was evaporated. A solution of the residue in 70 ml of diethyl ether was treated with 60 ml of water containing 2.5 g (0.025 mol) of potassium bicarbonate. 1.85 ml (0.023 mol) of benzyl chloroformate were added and the mixture was stirred vigorously for 1 hour. The organic solution was separated washed with 5% citric acid solution, water, 5% sodium bicarbonate solution and brine, dried over magnesium sulphate and evaporated to give a foam. Chromatography on 150 g of silica gel using n-hexane/ethyl acetate (2:1) yielded 4.4 g (53%) of Nα -(1-adamantylethyl)-Nα -benzyloxycarbonyl)-Nε -tert.butoxycarbonyl-L-lysyl-L-proline isobutylamide as a foam; Rf-value [n-hexane/ethyl acetate (2:1)]: 0.49.

Workup

  1. customcap
  2. customThe catalyst was removed by filtration
  3. customthe filtrate was evaporated
  4. customThe organic solution was separated
  5. washwashed with 5% citric acid solution, water, 5% sodium bicarbonate solution and brine
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customto give a foam

Sources & evidence

ORD record
ord-7638ecf506864237bda42bc09cddc02d
Source dataset
uspto-grants-1986_11
Patent number
US04623639

Linked notes

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