Acetic Acid → HCID 20739833, compound

HRID 1883501Notes

Reaction equation

HRID 1883501 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(OC(=O)[NH:17][C@@H:18]([CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)[C:19](=[O:31])[NH:20][CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28](=[NH:30])[CH3:29])[CH2:24][CH2:23]1)C1C=CC=CC=1.C(O)(=O)C>CO.[Pd]>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:17][C@@H:18]([CH:32]1[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1)[C:19]([NH:20][CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28](=[NH:30])[CH3:29])[CH2:24][CH2:23]1)=[O:31]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 69759278HCID 69759278, compound

Product 1

HCID 20739833HCID 20739833, compoundYield 113.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-(Cyclohexyl-{[1-(1-imino-ethyl)-piperidin-4-ylmethyl]-carbamoyl}-methyl)-carbamic acid benzyl ester trifluoroacetic acid salt (340 mg, 0.62 mmol) was hydrogenated in methanol (50 ml) and acetic acid (3 ml) using palladium/charcoal (10%) as a catalyst. The solvent was evaporated and the residue solved in water and lyophilized to give 287 mg of the desired product (88%). MS m/z: 295.4 (M+H)+.

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-3bda9ec2654f4700a790afcc8def87d1
Source dataset
uspto-grants-2004_07
Patent number
US06759420B1

Reaction notes

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