Dichloromethane → 2-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-ylmethyl)-2-methyl-malonic acid monoethyl ester

HRID 1789820Notes

Reaction equation

HRID 1789820 reaction equation
[Na].[C:2]([O:6][C:7]([N:9]([C:17]1[C:22]([CH3:23])=[CH:21][C:20]([CH2:24][C:25]2([CH3:35])[C:30](=[O:31])[O:29][C:28](C)([CH3:32])[O:27][C:26]2=[O:34])=[CH:19][N:18]=1)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:8])([CH3:5])([CH3:4])[CH3:3].C(Cl)Cl>C(O)C>[CH2:28]([O:27][C:26](=[O:34])[C:25]([CH2:24][C:20]1[CH:19]=[N:18][C:17]([N:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:7]([O:6][C:2]([CH3:5])([CH3:3])[CH3:4])=[O:8])=[C:22]([CH3:23])[CH:21]=1)([CH3:35])[C:30]([OH:31])=[O:29])[CH3:32]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 5360545SodiumHCID 220361342-[N,N-bis(tert-butoxycarbonyl)amino]-3-methyl-5-(2,2,5-trimethyl-4,6-dioxo-[1,3]dioxan-5-ylmethyl)-pyridin

Product 1

HCID 541480032-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-ylmethyl)-2-methyl-malonic acid monoethyl esterYield 101.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of sodium metal (184 mg, 8.0 mmol) in ethanol (20 mL) was added to a solution of 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, ˜4.0 mmol) in ethanol (20 mL) under argon. The reaction was stirred for 60 min. and methylene chloride was then added. The mixture was washed with 0.5 M HCl and brine, dried and concented under reduced pressure to give crude 2-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-ylmethyl)-2-methyl-malonic acid monoethyl ester (1.9 g)

Workup

  1. washThe mixture was washed with 0.5 M HCl and brine
  2. customdried

Sources & evidence

ORD record
ord-959be78dd6ce41cfb97af2d09627fb54
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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