Glycine tert-butyl ester → HCID 90281924, compound

HRID 1497545Notes

Reaction equation

HRID 1497545 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[O:6][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=O.[NH2:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].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:11]([O:10][C:8](=[O:9])[CH2:7][O:6][C:5]1[CH:4]=[C:3]([CH:17]=[CH:16][CH:15]=1)[CH2:1][NH:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 151417Glycine tert-butyl esterHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 14971816tert-Butyl (3-formylphenoxy)acetate

Product 1

HCID 90281924HCID 90281924, compoundYield 52.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of tert-butyl (3-formylphenoxy)acetate (1.50 g) in dichloroethane (20.0 mL) were added tert-butyl glycinate (874 mg) and acetic acid (1.09 mL), and then sodium triacetoxyborohydride (2.69 g) was added thereto under ice-cooling. The reaction suspension was stirred at room temperature for 16 hours. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol) to obtain tert-butyl N-[3-(2-tert-butoxy-2-oxoethoxy)benzyl]glycinate (1.18 g).

Workup

  1. temperatureunder ice-cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-822cc138dfc34e33bbf1060376a1bfef
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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