HCID 86706369, compound → HCID 66546513, compound

HRID 1396932Notes

Reaction equation

HRID 1396932 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:38][N:39]([CH:48]=[O:49])[O:40]CC2C=CC=CC=2)[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][N:21]=[C:20]([CH2:24][N:25]([CH3:27])[CH3:26])[N:19]=3)=[O:16])[CH2:13][CH2:12][N:11]2C(OCC2C=CC=CC=2)=O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1>[OH-].[OH-].[Pd+2].CO>[CH:1]1([CH2:6][C@H:7]([CH2:38][N:39]([CH:48]=[O:49])[OH:40])[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][N:21]=[C:20]([CH2:24][N:25]([CH3:26])[CH3:27])[N:19]=3)=[O:16])[CH2:13][CH2:12][NH:11]2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 86706369HCID 86706369, compound

Product 1

HCID 66546513HCID 66546513, compoundYield 58.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-[({2-[(dimethylamino)methyl]-4-pyrimidinyl}amino)carbonyl]-1-pyrazolidine carboxylate (104 mg, 0.155 mmol) and Pearlman's catalyst (21.74 mg, 0.031 mmol) in methanol (8.6 ml) was degassed and placed under 1 atm of H2 at ambient temperature. After 2 hrs, the reaction mixture was filtered and concentrated to give a residue which was purified by RP-HPLC to give (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-{2-[(dimethyl amino)methyl]-4-pyrimidinyl}-3-pyrazolidine carboxamide (41 mg, 0.090 mmol, 58% yield). MS (ES+) m/z 448.2 (MH+).

Workup

  1. customwas degassed
  2. customplaced under 1 atm of H2 at ambient temperature
  3. filtrationthe reaction mixture was filtered
  4. concentrationconcentrated
  5. customto give a residue which
  6. customwas purified by RP-HPLC

Sources & evidence

ORD record
ord-0e1ba0018a4c40caac647ccb66007251
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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