Water → Ethyl 3-(benzyloxy)-4-oxo-6,7,8,9-tetrahydro-4H-7,10-ethanopyrimido[1,2-a][1,3]diazepine-2-carboxylate

HRID 1093119Notes

Reaction equation

HRID 1093119 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13](S(C)(=O)=O)[C:12]([N:20]2[CH2:25][CH2:24][CH:23]([CH2:26]OS(C)(=O)=O)[CH2:22][CH2:21]2)=[N:11][C:10]=1[C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].O>C(O)C>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH2:26][CH:23]3[CH2:24][CH2:25][N:20]([C:12]2=[N:11][C:10]=1[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:21][CH2:22]3)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 57904840Ethyl 5-(benzyloxy)-1-(methylsulfonyl)-2-(4-((methylsulfonyloxy)methyl)piperidin-1-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate

Product 1

HCID 57904901Ethyl 3-(benzyloxy)-4-oxo-6,7,8,9-tetrahydro-4H-7,10-ethanopyrimido[1,2-a][1,3]diazepine-2-carboxylateYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 5-(benzyloxy)-1-(methylsulfonyl)-2-(4-((methylsulfonyloxy)methyl)piperidin-1-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate and K2CO3 (0.051 g, 0.368 mmol) in ethanol (10 mL) was stirred at 60° C. for 4 h and cooled to room temperature. Water was added and the product was extracted with ethyl acetate. The organic phase was washed with brine then dried (Na2SO4), filtered and concentrated. The residue was purified by flash column chromatography (Biotage flash chromatography system; 0%-10% methanol/CH2Cl2, 25 CV; 10% methanol/CH2Cl2, 5 CV) to give the title compound as a white glass (0.0248 g, 37% yield). 1H NMR (500 MHz, CDCl3) δ: 7.44 (2H, dd, J=7.3 Hz), 7.30-7.22 (3H, m), 5.27 (2H, s), 4.22 (2H, q, J=7.1 Hz), 4.01-3.94 (2H, m), 3.77-3.70 (2H, m), 3.67 (2H, brs), 3.02 (1H, brs), 2.29-2.24 (2H, m), 1.93-1.88 (2H, m), 1.22 (3H, t, J=7.0 Hz). LCMS (M+H) calcd for C20H24N3O4: 370.17; found: 370.30.

Workup

  1. temperaturecooled to room temperature
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialthen dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (Biotage flash chromatography system; 0%-10% methanol/CH2Cl2, 25 CV; 10% methanol/CH2Cl2, 5 CV)

Sources & evidence

ORD record
ord-70d3af1f637249cd96fa588b809a33e0
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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