Sodium Hydroxide → HCID 71227223, compound

HRID 713436Notes

Reaction equation

HRID 713436 reaction equation
C[O:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12](=[O:30])[N:13]([CH2:26][CH:27]2[CH2:29][CH2:28]2)[CH2:14][C:15]2[NH:16][C:17](=[O:25])[CH:18]3[CH2:24][O:23][CH2:22][CH2:21][CH:19]3[N:20]=2)[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+]>CO.O>[CH:27]1([CH2:26][N:13]([CH2:14][C:15]2[NH:16][C:17](=[O:25])[CH:18]3[CH2:24][O:23][CH2:22][CH2:21][CH:19]3[N:20]=2)[C:12]([CH2:11][N:8]2[CH2:7][CH2:6][CH:5]([C:3]([OH:4])=[O:2])[CH2:10][CH2:9]2)=[O:30])[CH2:28][CH2:29]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 71226888HCID 71226888, compound

Product 1

HCID 71227223HCID 71227223, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-{[cyclopropylmethyl-(4-oxo-3,4a,5,7,8,8a-hexahydro-4H-pyrano[4,3-d]pyrimidin-2-ylmethyl)-carbamoyl]-methyl}-piperidine-4-carboxylic acid methyl ester (0.6 g, 1.43 mmol, 1 eq.) in 3 mL of MeOH was added a solution of NaOH (0.13 g, 5.43 mmol, 3.8 eq.) in 3 mL of H2O. The resulting mixture was stirred at room temperature overnight. After 18 h, the reaction mixture was concentrated and treated with 1 N HCl to pH 5. The resulting mixture was freeze dried using lyophilizer to remove H2O. The resulting white solids were washed with dichloromethane/methanol and filtered to remove NaCl. The filtrate was concentrated to give the title compound as a white solid (0.53 g, 92%). Exact mass calculated for C23H31N4O3 407.2. MS (ESI) m/z 407.6 (M+H)+.

Workup

  1. waitAfter 18 h
  2. concentrationthe reaction mixture was concentrated
  3. additiontreated with 1 N HCl to pH 5
  4. customdried
  5. customto remove H2O
  6. washThe resulting white solids were washed with dichloromethane/methanol
  7. filtrationfiltered
  8. customto remove NaCl
  9. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b7a0aa0f1a454266b466b407647e387f
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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