Ethanol sodium ethoxide → HCID 58962289, compound

HRID 1365729Notes

Reaction equation

HRID 1365729 reaction equation
CS([O:5][C:6]1[C:15](=[O:16])[N:14]2[C:9]([C:10]3([CH2:20][CH2:19][CH2:18][CH2:17]3)[O:11][CH2:12][CH2:13]2)=[N:8][C:7]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22])(=O)=O.CC[O-].[Na+].CCO>C1COCC1>[OH:5][C:6]1[C:15](=[O:16])[N:14]2[C:9]([C:10]3([CH2:20][CH2:19][CH2:18][CH2:17]3)[O:11][CH2:12][CH2:13]2)=[N:8][C:7]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

4

Reactant 2

HCID 23706232Ethanol sodium ethoxideHCID 58962311HCID 58962311, compound

Product 1

HCID 58962289HCID 58962289, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of ethyl 3′-(methylsulfonyloxy)-4′-oxo-6′,7′-dihydro-4′H-spiro[cyclopentane-1,9′-pyrimido[2,1-c][1,4]oxazine]-2′-carboxylate (0.6861 g, 1.84 mmol) in THF (50 mL) was added 1M EtONa/EtOH (10 mL). After 1 h, the resulting yellow solution was concentrated, acidified with 1 M aq. HCl (20 mL), extracted with CH2Cl2 (3×35 mL). The combined organic layers dried (Na2SO4), filtered and concentrated to give the title compound as a brown solid (0.4668 g, 86%). 1H NMR (500 MHz, CDCl3) δ: 10.49 (1H, s), 4.44 (2H, q, J=7.0 Hz), 4.03-3.97 (4H, m), 2.28-2.22 (2H, m), 2.06-2.01 (2H, m), 1.93-1.81 (4H, m), 1.42 (3H, t, J=7.0 Hz). HRMS (M+H) calcd for C14H19N2O5: 295.1294; found: 295.1293.

Workup

  1. concentrationthe resulting yellow solution was concentrated
  2. extractionextracted with CH2Cl2 (3×35 mL)
  3. dry with materialThe combined organic layers dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ccc50472be7a4f4fa2b990230068c13f
Source dataset
uspto-grants-2011_02
Patent number
US07893055B2

Reaction notes

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