Glycine methyl ester hydrochloride → Methyl (2-((tert-butoxycarbonyl)amino)ethyl)glycinate

HRID 1735950Notes

Reaction equation

HRID 1735950 reaction equation
[C:1](C(N)C=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:12]([O-])(=O)[CH3:13].[Na+].Cl.[CH3:18][O:19][C:20](=[O:23])[CH2:21][NH2:22].C([BH3-])#[N:25].[Na+]>CO.O>[CH3:18][O:19][C:20](=[O:23])[CH2:21][NH:22][CH2:13][CH2:12][NH:25][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

7

Reactant 4

HCID 122755Glycine methyl ester hydrochlorideHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 57245992HCID 57245992, compound

Product 1

HCID 10889780Methyl (2-((tert-butoxycarbonyl)amino)ethyl)glycinateYield 34%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Boc-aminoacetaldehyde (19, 1.00 g, 6.3 mmol, 1 eqv) was dissolved in methanol (50 ml). Anhydrous sodium acetate (1.03 g, 12.6 mmol, 2 eqv), glycine methyl ester hydrochloride (Aldrich Chemical Co., 0.79 g, 6.3 mmol, 1 eqv) and sodium cyanoborohydride (1.97 g, 31.4 mmol, 5 eqv) were added to the solution in that order. The reaction mixture was stirred for 2 h at room temperature under nitrogen. Water (50 ml) was added to the suspension and the resulting clear solution was evaporated under reduced pressure to remove the methanol. The aqueous phase was extracted with methylene chloride (3×100 ml). The organic phase was washed with a saturated aqueous solution of sodium chloride (1×100 ml), dried (Na2SO4), filtered and then evaporated under reduced pressure affording 1.41 g of crude title compound as a yellow oil. The crude product was kugelrohr distilled at 110° C. and 0.5 mbar to yield 0.49 g (34%) of 2-(Boc-amino)ethylglycine methyl ester as a colorless liquid. 1H-NMR (CDCl3 /TMS): δ=1.36 (s, 9H, Me3C), 1.91 (s, 1H, NH), 2.67 (t, J=6 Hz, 2H, NHCH2), 3.13 (q, J=6 Hz, 2H, NHCH2), 3.34 (s, 2H, CH2CO0), 3.65 (s, 3H, OMe), 5.13 (b, 1H, carbamate NH). 13C-NMR (CDCl3 /TMS): δ=28.2 (Me3C), 39.9, 48.5 (NHCH2), 50.0 (CH2COO), 51.5 (OMe), 78.9 (Me3C), 155.9 (carbamate C=O), 172.6 (ester C=O). Anal. Calcd for C10H2N2O4 : C, 51.71; H, 8.68; N, 12.06. Found: C, 51.55; H, 8.72; N, 11.79.

Workup

  1. customthe resulting clear solution was evaporated under reduced pressure
  2. customto remove the methanol
  3. extractionThe aqueous phase was extracted with methylene chloride (3×100 ml)
  4. washThe organic phase was washed with a saturated aqueous solution of sodium chloride (1×100 ml)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customaffording 1.41 g of crude title compound as a yellow oil
  9. distillationThe crude product was kugelrohr distilled at 110° C.

Sources & evidence

ORD record
ord-3bf3f60a9cf341e8bf1b1a7de8a8aa2f
Source dataset
uspto-grants-1996_07
Patent number
US05539082

Reaction notes

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