Water → 2-[N,N-bis(tert-butoxycarbonyl)amino]-3-methyl-5-(2,2,5-trimethyl-4,6-dioxo-[1,3]dioxan-5-ylmethyl)-pyridin

HRID 1789819Notes

Reaction equation

HRID 1789819 reaction equation
[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([CH3:22])=[CH:20][C:19]([CH2:23]Br)=[CH:18][N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25][C:26]1([CH3:35])[O:31][C:30](=[O:32])[CH:29]([CH3:33])[C:28](=[O:34])[O:27]1.C(N(CC)CC)C.O>CS(C)=O>[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([CH3:22])=[CH:20][C:19]([CH2:23][C:29]2([CH3:33])[C:28](=[O:34])[O:27][C:26]([CH3:25])([CH3:35])[O:31][C:30]2=[O:32])=[CH:18][N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 772992,2,5-Trimethyl-1,3-dioxane-4,6-dioneHCID 220360092-[N,N-bis(tert-Butoxycarbonyl)amino]-5-bromomethyl-3-methyl-pyridin

Product 1

HCID 220361342-[N,N-bis(tert-butoxycarbonyl)amino]-3-methyl-5-(2,2,5-trimethyl-4,6-dioxo-[1,3]dioxan-5-ylmethyl)-pyridinYield 107.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-[N,N-bis(tert-Butoxycarbonyl)amino]-5-bromomethyl-3-methyl-pyridin (1.6 g, 4.0 mmol) was added to a solution of 2,2,5-trimethyl-1,3-dioxane-4,6-dione (630 mg, 4.0 mmol) and triethylamine (0.58 mL, 4.2 mmol) in dimethyl sulfoxide (40 mL). The reaction mixture was stirred overnight and water (100 mL) was added. The mixture was extracted with EtOAc, the combined organic phases washed with water and brine and dried. Concentration under reduced pressure gave crude 2-[N,N-bis(tert-butoxycarbonyl)amino]-3-methyl-5-(2,2,5-trimethyl-4,6-dioxo-[1,3]dioxan-5-ylmethyl)-pyridin (2.06 g)

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washthe combined organic phases washed with water and brine
  3. customdried
  4. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-9eb117af31054614bd2029b09386dfab
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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