Hydrochloric Acid → HCID 136061310, compound

HRID 1093066Notes

Reaction equation

HRID 1093066 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:22]2[NH:23][C:24](=[O:34])[C:25]([OH:33])=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:27]=2)[CH2:21][CH2:20][C:15]2(OCC[O:16]2)[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1>[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:22]2[NH:23][C:24](=[O:34])[C:25]([OH:33])=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:27]=2)[CH2:21][CH2:20][C:15](=[O:16])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 136061309HCID 136061309, compound

Product 1

HCID 136061310HCID 136061310, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of ethyl 2-(8-(benzyloxycarbonylamino)-1,4-dioxaspiro[4.5]decan-8-yl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate (1.8 g, 3.8 mmol) in THF (200 mL) was added 2N HCl (12 ml, 24 mmol) and the resulting mixture was heated for 2 h at 60° C. The reaction mixture was then cooled and extracted with CH2Cl2 (3×100 mL). The CH2Cl2 fractions were dried (Na2SO4), filtered and concentrated to afford the title compound as a light yellow solid (1.5 g, 92% yield). 1H NMR (500 MHz, CDCl3) δ: 12.11 (s, 1H), 11.09 (s, 1H), 7.17-7.29 (m, 5H), 6.36 (s, 1H), 5.00 (s, 2H), 4.44 (q, 2H, J=7.02 Hz), 2.49-2.57 (m, 8H), 1.42 (q, 3H, J=7.05 Hz). LCMS (M+H)=430.38.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. extractionextracted with CH2Cl2 (3×100 mL)
  3. dry with materialThe CH2Cl2 fractions were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4bc99eecfcf34c8691b1b58b157e0c9d
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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