methyl N-(2-chloro-5-nitropyrimidin-4-yl)-N-1,4-d ioxaspiro[4.5]dec-8-yl-D-alaninate → HCID 89561481, compound

HRID 530117Notes

Reaction equation

HRID 530117 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH:15]2[CH2:24][CH2:23][C:18]3(OCC[O:19]3)[CH2:17][CH2:16]2)[C@@H:9]([C:11]([O:13][CH3:14])=[O:12])[CH3:10])[C:5]([N+:25]([O-:27])=[O:26])=[CH:4][N:3]=1>O1CCOCC1>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH:15]2[CH2:24][CH2:23][C:18](=[O:19])[CH2:17][CH2:16]2)[C@@H:9]([C:11]([O:13][CH3:14])=[O:12])[CH3:10])[C:5]([N+:25]([O-:27])=[O:26])=[CH:4][N:3]=1

Participants

3

Reactant 1

HCID 89570510methyl N-(2-chloro-5-nitropyrimidin-4-yl)-N-1,4-d ioxaspiro[4.5]dec-8-yl-D-alaninate

Product 1

HCID 89561481HCID 89561481, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirred solution of methyl N-(2-chloro-5-nitropyrimidin-4-yl)-N-1,4-dioxaspiro[4.5]dec-8-yl-D-alaninate (17 g, 42.5 mmol) in dioxane (450 mL, contains 1M HCl) was heated to reflux for 16 h. The bulk of solvent was then removed under reduced pressure, the crude material was neutralized with aq. NaHCO3, and extracted with ethyl acetate (300 mL×3). Organic layers were combined, dried over sodium sulfate, and evaporated to give the crude material, which was then purified by silica gel column chromatography to give the desired product (10 g). 1HNMR (300 MHz, CDCl3): δ 1.66 (d, J=6.9 Hz, 3H), 1.99-2.18 (m, 2H), 2.34-2.57 (m, 6H), 3.56-3.59 (m, 1H), 3.76 (s, 3H), 4.04 (q, J=6.9, 13.8 Hz, 1H), 8.70 (s, 1H).

Workup

  1. temperatureto reflux for 16 h
  2. customThe bulk of solvent was then removed under reduced pressure
  3. extractionextracted with ethyl acetate (300 mL×3)
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto give the crude material, which
  7. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-74081699661e4030845239e48d896fa4
Source dataset
uspto-grants-2016_05
Patent number
US09351974B2

Reaction notes

Loading…