1,4-Cyclohexadiene → HCID 86654760, compound

HRID 447137Notes

Reaction equation

HRID 447137 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]([NH:5][C@@H:6]([CH2:23][CH3:24])[C:7]([NH:9][CH2:10][CH2:11][NH:12]C(=O)OCC1C=CC=CC=1)=[O:8])=[O:4].C1CC=CCC=1>C(O)C.[Pd]>[NH2:12][CH2:11][CH2:10][NH:9][C:7](=[O:8])[C@@H:6]([NH:5][C:3](=[O:4])[C:2]([F:26])([F:1])[F:25])[CH2:23][CH3:24]

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 86654761HCID 86654761, compound

Product 1

HCID 86654760HCID 86654760, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a heterogenous mixture of (S)-benzyl 2-(2-(2,2,2-trifluoroacetamido)butanamido)ethylcarbamate (1.1913 g, 3.20 mmol) and 10% Pd on carbon (1.2236 g) in ethanol (75 mL) was added 1,4-cyclohexadiene (3.0 mL, 32.0 mmol). The resulting mixture was stirred overnight at room temperature. The resulting mixture was then filtered through a bed of CELITE® and concentrated. The residue was dissolved in chloroform and filtered again through CELITE® to yield (S)—N-(2-aminoethyl)-2-(2,2,2-trifluoroacetamido)butanamide as an unstable oil which was stored in the freezer.

Workup

  1. filtrationThe resulting mixture was then filtered through a bed of CELITE®
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in chloroform
  4. filtrationfiltered again through CELITE®

Sources & evidence

ORD record
ord-deab92254d864de1a6e2e6e3420832c6
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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