Water → HCID 66546325, compound

HRID 1396929Notes

Reaction equation

HRID 1396929 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:26][N:27]([CH:35]=[O:36])[O:28]C2CCCCO2)[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[N:23]=[CH:22][C:21]([O:24][CH3:25])=[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.O>C(O)(=O)C>[CH:1]1([CH2:6][C@H:7]([CH2:26][N:27]([CH:35]=[O:36])[OH:28])[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[N:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][N:23]=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 962WaterHCID 86706367HCID 86706367, compound

Product 1

HCID 66546325HCID 66546325, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}propanoyl)-N-[5-(methyloxy)-2-pyrimidinyl]-3-pyrazolidinecarboxamide (67 mg, 0.133 mmol) in acetic acid (7 ml)/water (1.8 ml) was stirred at ambient temperature for overnight. The solvent was removed to give a residue which was purified by RP-HPLC to give (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-[5-(methyloxy)-2-pyrimidinyl]-3-pyrazolidinecarboxamide (27 mg, 0.061 mmol, 46% yield). MS (ES+) m/z 421.1 (MH+).

Workup

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

Sources & evidence

ORD record
ord-595a01d12b1a4084b5d0fcd73b24d4fb
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

Loading…