benzyl (2S,4S)-2-[(4-{[(2-methyl-2-propanyl)oxy]carbonyl}phenyl)carbamoyl]-4-[4-(methylsulfonyl)-1-piperazinyl]-1-pyrrolidinecarboxylate → 2-methyl-2-propanyl 4-[({(2S,4S)-4-[4-(methylsulfonyl)-1-piperazinyl]-2-pyrrolidinyl}carbonyl)amino]benzoate

HRID 1053813Notes

Reaction equation

HRID 1053813 reaction equation
[CH3:1][C:2]([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([C@@H:17]2[CH2:21][C@H:20]([N:22]3[CH2:27][CH2:26][N:25]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][CH2:23]3)[CH2:19][N:18]2C(OCC2C=CC=CC=2)=O)=[O:16])=[CH:10][CH:9]=1)=[O:7])([CH3:4])[CH3:3]>C(O)C.[Pd]>[CH3:31][S:28]([N:25]1[CH2:26][CH2:27][N:22]([C@@H:20]2[CH2:19][NH:18][C@H:17]([C:15]([NH:14][C:11]3[CH:12]=[CH:13][C:8]([C:6]([O:5][C:2]([CH3:1])([CH3:4])[CH3:3])=[O:7])=[CH:9][CH:10]=3)=[O:16])[CH2:21]2)[CH2:23][CH2:24]1)(=[O:30])=[O:29]

Participants

4

Reactant 1

HCID 122584929benzyl (2S,4S)-2-[(4-{[(2-methyl-2-propanyl)oxy]carbonyl}phenyl)carbamoyl]-4-[4-(methylsulfonyl)-1-piperazinyl]-1-pyrrolidinecarboxylate

Product 1

HCID 1181076652-methyl-2-propanyl 4-[({(2S,4S)-4-[4-(methylsulfonyl)-1-piperazinyl]-2-pyrrolidinyl}carbonyl)amino]benzoateYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the compound prepared in Example 5 (2.1 g, 7.4 mmol) in ethanol (100 mL) was added Pd/C (0.40 g, 20% by wt). The reaction was stirred under an atmosphere of hydrogen (50 psi) at room temperature for 6 h. The reaction mixture was filtered through diatomaceous earth and concentrated to give the title compound (1.10 g, 69%) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-0d458ab1ee6142938fcd82d65a638364
Source dataset
uspto-grants-2016_07
Patent number
US09394250B2

Reaction notes

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