Hydrochloric Acid → 8-(1-hydroxyethyl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylic acid

HRID 572805Notes

Reaction equation

HRID 572805 reaction equation
[OH-].[Na+].[OH:3][CH:4]([C:6]1[CH:7]=[C:8]([C:24]([O:26]C)=[O:25])[CH:9]=[C:10]2[C:15]=1[O:14][C:13]([N:16]1[CH2:21][CH2:20][O:19][C@H:18]([CH3:22])[CH2:17]1)=[CH:12][C:11]2=[O:23])[CH3:5].O.Cl>CO>[OH:3][CH:4]([C:6]1[CH:7]=[C:8]([C:24]([OH:26])=[O:25])[CH:9]=[C:10]2[C:15]=1[O:14][C:13]([N:16]1[CH2:21][CH2:20][O:19][C@H:18]([CH3:22])[CH2:17]1)=[CH:12][C:11]2=[O:23])[CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 58234968methyl 8-(1-hydroxyethyl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylate

Product 1

HCID 582349828-(1-hydroxyethyl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylic acidYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaOH (3.56 mL, 7.11 mmol) was added to a stirred suspension of methyl 8-(1-hydroxyethyl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylate (988 mg, 2.84 mmol) in MeOH (10 mL)/water (10 mL). The resulting mixture was stirred at RT for 1 hour then acidified to pH 2-3 with a 2N aq. HCl (7.68 mL, 7.68 mmol). The resulting precipitate was collected by filtration, washed with diethyl ether and dried to afford 8-(1-hydroxyethyl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylic acid (900 mg, 95%) as a grey solid, which was used without further purification. Mass Spectrum: M+H+ 334.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-cda6c2d8a8044da5935b7d99eeaf8f93
Source dataset
uspto-grants-2015_05
Patent number
US09029374B2

Reaction notes

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