phenylmethyl 1-[N-[4-(2-methyl-2-propyloxycarbonyl)piperazine-1-carbonyl]amino]cyclohexanecarboxylate → 1-[N-[4-(2-methyl-2-propyloxycarbonyl)piperazine-1-carbonyl]amino]cyclohexanecarboxylic acid

HRID 1953431Notes

Reaction equation

HRID 1953431 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([NH:16][C:17]2([C:23]([O:25]CC3C=CC=CC=3)=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])[CH3:3].[H][H]>C(O)C.[C].[Pd]>[CH3:4][C:2]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([NH:16][C:17]2([C:23]([OH:25])=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:1])[CH3:3]

Participants

5

Reactant 2

HCID 53984920phenylmethyl 1-[N-[4-(2-methyl-2-propyloxycarbonyl)piperazine-1-carbonyl]amino]cyclohexanecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 114941311-[N-[4-(2-methyl-2-propyloxycarbonyl)piperazine-1-carbonyl]amino]cyclohexanecarboxylic acidYield 94.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Further, 4.3 g (9.65 mmol) of the above phenylmethyl 1-[N-[4-(2-methyl-2-propyloxycarbonyl)piperazine-1-carbonyl]amino]cyclohexanecarboxylate was dissolved in 200 ml of ethanol and 400 mg of 10% palladium carbon was suspended thereinto and under air current of hydrogen stirred for 15 hours. The insoluble components were removed from the reaction mixture by filtration. The filtrate was concentrated under reduced pressure, whereby 3.25 g of the captioned 1-[N-[4-(2-methyl-2-propyloxycarbonyl)piperazine-1-carbonyl]amino]cyclohexanecarboxylic acid was obtained in a yield of 45%.

Workup

  1. customThe insoluble components were removed from the reaction mixture by filtration
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-668b042a30a44bb2a925afac02f9697d
Source dataset
uspto-grants-2000_09
Patent number
US06117870

Reaction notes

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