Hydrochloric Acid → HCID 13649260, compound

HRID 1200156Notes

Reaction equation

HRID 1200156 reaction equation
[CH3:1][C:2]([NH:10][C:11](=[O:37])[C@@H:12]([NH:28][C:29](=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:13][CH2:14][CH2:15][CH2:16][NH:17]C(OCC1C=CC=CC=1)=O)([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.[H][H]>C(O)C.[Pd]>[CH3:9][C:2]([NH:10][C:11](=[O:37])[C@@H:12]([NH:28][C:29](=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])([CH3:1])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 13649258HCID 13649258, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13649260HCID 13649260, compoundYield 106.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.73 g of (2S)-N-(α,α-dimethylbenzyl)-2-benzoylamino-6-(benzyloxycarbonylamino)hexanamide (prepared as described in Example 8) dissolved in 80 ml of ethanol and 4 ml of 1N hydrochloric acid was catalytically reduced by hydrogen gas in the presence of 0.33 g of 10% w/w palladium-on-carbon at room temperature. After filtering off the catalyst, the filtrate was concentrated by evaporation under reduced pressure to afford 1.35 g of the title compound as an amorphous substance melting at 94°-101° C. (with decomposition)

Workup

  1. filtrationAfter filtering off the catalyst
  2. concentrationthe filtrate was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-541dd2da36d743818500f6fa93fc59a7
Source dataset
uspto-grants-1990_02
Patent number
US04904680

Reaction notes

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