Sodium Bicarbonate → HCID 90282035, compound

HRID 1497516Notes

Reaction equation

HRID 1497516 reaction equation
[CH:1]([C:3]1[N:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=1)=O.Cl.[NH2:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClC(Cl)C.C(O)(=O)C.C(N(CC)CC)C>[C:20]([O:19][C:17](=[O:18])[CH2:16][NH:15][CH2:1][C:3]1[N:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

8

Reactant 4

HCID 516892Sodium Bicarbonate2×HCID 2725036Glycine tert-butyl ester hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 44206644Ethyl 6-formylpyridine-2-carboxylate

Product 1

HCID 90282035HCID 90282035, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 63651,1-DichloroethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of ethyl 6-formylpyridine-2-carboxylate (1.74 g) in dichloroethane (30.0 mL) were added tert-butyl glycinate hydrochloride (4.89 g), triethylamine (4.06 mL), and acetic acid (2.78 mL), and sodium triacetoxyborohydride (6.18 g) under ice-cooling. The reaction suspension was stirred at room temperature overnight. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and then sodium hydrogen carbonate was added thereto until the solution became basic. The reaction mixture was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane-ethyl acetate) to obtain ethyl 6-{[(2-tert-butoxy-2-oxoethyl)amino]methyl}pyridine-2-carboxylate (2.83 g).

Workup

  1. temperaturecooling
  2. extractionThe reaction mixture was extracted with chloroform
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-e5bc7a3b84314ca09547d2c2726b2d88
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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