Sodium Hydroxide → 6-[(3-{[(Benzyloxy)carbonyl](methyl)amino}propyl)(methyl)carbamoyl]pyridine-3-carboxylic acid

HRID 446505Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]([CH3:29])[CH2:12][CH2:13][CH2:14][N:15]([CH3:28])[C:16]([C:18]1[N:23]=[CH:22][C:21]([C:24]([O:26]C)=[O:25])=[CH:20][CH:19]=1)=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([O:8][C:9]([N:11]([CH3:29])[CH2:12][CH2:13][CH2:14][N:15]([CH3:28])[C:16]([C:18]1[N:23]=[CH:22][C:21]([C:24]([OH:26])=[O:25])=[CH:20][CH:19]=1)=[O:17])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

The compound (1.23 g, 3.08 mmol) obtained in Example 5a was dissolved in methanol (9 mL), a 1 N aqueous sodium hydroxide solution (9.24 mL, 9.24 mmol) was added, and then the mixture was stirred at 50° C. for 10 hours. The solvent was evaporated under reduced pressure, ethyl acetate was added to the resulting residue, the mixture was extracted with water (×2), the aqueous layer was adjusted to pH 3 with 1 N hydrochloric acid, and the mixture was extracted with methylene chloride (×3) and dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (799 mg; yield, 68%) as a colorless oily substance.

Workup

customThe solvent was evaporated under reduced pressure, ethyl acetate
additionwas added to the resulting residue
extractionthe mixture was extracted with water (×2)
extractionthe mixture was extracted with methylene chloride (×3)
dry with materialdried with anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-b8efe9554d574af5a563aa38c1618614
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476253B2

Reaction notes

Loading…