HCID 70493071, compound → HCID 86741121, compound

HRID 1731974Notes

Reaction equation

HRID 1731974 reaction equation
C[O:2][CH:3](OC)[C@H:4]([CH:53]([CH3:55])[CH3:54])[NH:5][C:6](=[O:52])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:51])[C@H:13]([CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:33](=[O:50])[C:34]1[CH:39]=[CH:38][C:37]([C:40]([O:42]CC2C=CC=CC=2)=[O:41])=[CH:36][CH:35]=1)[NH:14][S:15]([C:18]12[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2)(=[O:17])=[O:16]>CN(C)C=O.C(=O)(O)[O-].[Na+].[Pd]>[C:18]12([S:15]([NH:14][C@H:13]([C:12]([N:8]3[CH2:9][CH2:10][CH2:11][C@H:7]3[C:6]([NH:5][C@H:4]([CH:3]=[O:2])[CH:53]([CH3:55])[CH3:54])=[O:52])=[O:51])[CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:33](=[O:50])[C:34]3[CH:39]=[CH:38][C:37]([C:40]([OH:42])=[O:41])=[CH:36][CH:35]=3)(=[O:16])=[O:17])[CH2:19][CH:20]3[CH2:21][CH:22]([CH2:23][CH:24]([CH2:26]3)[CH2:25]1)[CH2:27]2

Participants

5

Reactant 1

HCID 70493071HCID 70493071, compound

Product 1

HCID 86741121HCID 86741121, compoundYield 33%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

1.3 g (1.6 mmol) of Nα -(1-adamantylsulphonyl)-Nε -(4-benzyloxycarbonylbenzoyl)-L-lysyl-L-prolyl-L-valinal dimethyl acetal in 15 ml of dimethylformamide were hydrogenated in the presence of 5% palladium/carbon for 3 hours. The catalyst was removed by filtration and the filtrate was evaporated to give an oil. This oil was taken up in sodium bicarbonate solution, extracted with ethyl acetate, the aqueous phase was acidified to pH 2-3 with dilute hydrochloric acid and extracted with ethyl acetate. The organic phase was washed free from acid with water, dried over magnesium sulphate and evaporated to give a foam. This foam was chromatographed on 25 g of silica gel using dichloromethane/methanol/acetic acid (190:9:2) for the elution. Evaporation of the eluate and trituration of the residue with diethyl ether yielded 0.35 g (33%) of Nα -(1-adamantylsulphonyl)-Nε -(4-carboxybenzoyl)-L-lysyl-L-prolyl-L-valinal in the form of a solid.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. customto give an oil
  4. extractionextracted with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe organic phase was washed free from acid with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. customto give a foam
  10. customThis foam was chromatographed on 25 g of silica gel
  11. washfor the elution
  12. customEvaporation of the eluate and trituration of the residue with diethyl ether

Sources & evidence

ORD record
ord-60729826b7d24fc4b7f94cf0e16075f3
Source dataset
uspto-grants-1986_11
Patent number
US04623639

Reaction notes

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