Acetic Acid → HCID 66546322, compound

HRID 1396918Notes

Reaction equation

HRID 1396918 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:24][N:25]([CH:33]=[O:34])[O:26]C2CCCCO2)[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[N:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[O:16])[CH2:13][CH2:12][NH:11]2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(=O)C>O>[CH:1]1([CH2:6][C@H:7]([CH2:24][N:25]([CH:33]=[O:34])[OH:26])[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[N:23]=[CH:22][CH:21]=[CH:20][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 2

HCID 176Acetic AcidHCID 86706361HCID 86706361, compound

Product 1

HCID 66546322HCID 66546322, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}propanoyl)-N-2-pyrimidinyl-3-pyrazolidinecarboxamide (20 mg, 0.042 mmol) in the solution of Acetic Acid (2 ml) and Water (0.500 ml) was stirred at 25° C. for overnight. The solvent was removed to give a residue. The residue was purified by RP-HPLC to give (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-2-pyrimidinyl-3-pyrazolidine carboxamide (9 mg, 0.023 mmol, 54% yield). MS (ES+) m/z 391.3 (MH+).

Workup

  1. customThe solvent was removed
  2. customto give a residue
  3. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-0002595f102e4450a032a7d6729fe146
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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