Hydrochloric Acid → HCID 86724971, compound

HRID 1847046Notes

Reaction equation

HRID 1847046 reaction equation
COC[CH2:4][C@@H:5]1[CH2:9][N:8]([C:10]2[CH:11]=[CH:12][C:13]3[O:14][CH2:15][C:16](=[O:20])[NH:17][C:18]=3[N:19]=2)[C:7](=[O:21])[CH2:6]1.[O:22]1CCCC1.Cl.C(=O)([O-])O.[Na+]>CO>[OH:22][CH2:4][C@@H:5]1[CH2:9][N:8]([C:10]2[CH:11]=[CH:12][C:13]3[O:14][CH2:15][C:16](=[O:20])[NH:17][C:18]=3[N:19]=2)[C:7](=[O:21])[CH2:6]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 86724972HCID 86724972, compound

Product 1

HCID 86724971HCID 86724971, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6-{(4S)-4-[(methoxymethyl)methyl]-2-oxopyrrolidin-1-yl}-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (2.21 g, 7.20 mmol) in methanol (25 ml)/tetrahydrofuran (25 ml) was added 4N Hydrochloric acid (2.5 ml) at room temperature and the mixture was heated to 60° C. and stirred with heating for 16 hours. The reaction solution was poured into a saturated sodium hydrogen carbonate aqueous solution and extracted with a mixed solvent of chloroform/methanol (9:1) (3×). The organic layer was dried over anhydrous sodium sulfate, the drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. 1.76 g (93%) of a crude product of the title compound was obtained in the form of a light yellow solid.

Workup

  1. temperaturewith heating for 16 hours
  2. extractionextracted with a mixed solvent of chloroform/methanol (9:1) (3×)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe drying agent was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8ff50747d5f343138d9896bacff4fb80
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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