[(tert-Butoxycarbonyl)(methyl)amino]acetic acid

white crystals or crystalline powder

Triethylamine (23.5 mL, 168.3 mmol) and di-tert-butyl dicarbonate (12.9 mL, 56.1 mmol) were added sequentially to a solution of sarcosine (5.0 g, 56.1 mmol) in HTo a 250 mL round bottom flask containing sarcosine (1.78 g, 20 mmol, 1.0 eq. ), H20 (20 mL), and dioxane (40 mL) was added a solution of sodium hydroxide (3.6 g in 6 mL of H2O, 4.5 eq. ). The reaction flask was then cooled to 0°C before Boc- anhydride (5.2 g, 24.0 mmol, 1.2 eq. ) was added in one portion. The reaction was then stirred overnight at RT before concentrating via rotary evaporation to remove dioxane. The remaining aqueous solution was then extracted with EtOAc (40 mL). The EtOAc layer was discarded, and the aqueous layer was acidified with 1N HC1 until pH = 3. The aqueous layer was then extracted three times with EtOAc. The combined organic layers were then washed with brine, dried with Na2S04, and concentrated to yield Boc-sarcosine as a clear oil (3.5 g, 92percent). 1H-NMR (d6-DMSO) : 3.83 (d, 2H), 2.80 (d, 3H), 1.39 (d, 9H) ppm.To a 250 mL round bottom flask containing sarcosine (1.78 g, 20 mmol, 1.0 eq. ), H20 (20 mL), and dioxane (40 mL) was added a solution of sodium hydroxide (3.6 g in 6 mL of H2O, 4.5 eq. ). The reaction flask was then cooled to 0°C before Boc- anhydride (5.2 g, 24.0 mmol, 1.2 eq. ) was added in one portion. The reaction was then stirred overnight at RT before concentrating via rotary evaporation to remove dioxane. The remaining aqueous solution was then extracted with EtOAc (40 mL). The EtOAc layer was discarded, and the aqueous layer was acidified with 1N HC1 until pH = 3. The aqueous layer was then extracted three times with EtOAc. The combined organic layers were then washed with brine, dried with Na2S04, and concentrated to yield Boc-sarcosine as a clear oil (3.5 g, 92percent). 1H-NMR (d6-DMSO) : 3.83 (d, 2H), 2.80 (d, 3H), 1.39 (d, 9H) ppm.To a mixture of sarcosine (13.4 g, 150 mmol) and Et3N (62.7 mL, 450 mmol) in H2O (750 mL)was added (Boc)2O (32.9 g, 151 mmol) at 0 °C. After stirring for 4 h at room temperature, thereaction was quenched by adding 3 M aqueous HCl, and the mixture was extracted with EtOAc(x8). The combined organic extracts were dried (Na2SO4), and concentrated in vacuo to affordamino acid S-1 (28.5 g, quant.) as a white solid. This material was used in the next step withoutfurther purificationGeneral procedure: (S)-2-(Tert-butoxycarbonyl(methyl)amino)-3-hydroxypropanoic acid(6a) Gummy substance (This compound was prepared byadding neat sodium hydride (10 equiv.) in portion wiseover a period of 2.0 h to a cooled (0 °C) solution of (S)-2-(tert-butoxycarbonylamino)-3-hydroxypropanoic acid (1equiv.) and iodomethane (10 equiv.) in dry THF under astream of nitrogen. The reaction mixture was stirred at room temperature for 24 h under nitrogen atmosphere andthen diluted with ether (20 mL) and quenched with water(30 mL). The layers were separated and the aqueous layerwas extracted with ether (2 x9 15 mL), acidified to pH 3with a 20 percent aqueous solution of citric acid and extractedwith EtOAc (3 x 20 mL). The combined organic phasewas dried over Na2SO4 and evaporated to afford thecorresponding N-methylated product in 90 percent yield asGummy substance.)Sodium hydride (6.85 g, 171 mmol) was added to a mixture of (fer/-butoxycarbonyl)glycine (10 g, 57.1 mmol) and methyl iodide (75 g, 528 mmol) in THF (600 mL) at 0 °C. The mixture was slowly allowed to warm to rt overnight. Water (300 mL) was added and extracted into ethyl acetate (2 x 500 mL). The aqueous layer was acidified to pH 3 with 1 M Hci extracted with ethyl acetate (2 x 500 mL). The combined organic layer was extracted with saturated aqueous sodium chloride (500 mL), dried (MgSO^, filtration and concentrated to give the title compound as an oil (10 g, 91 percent).Sodium hydride (6.85 g, 171 mmol) was added to a mixture of (tert-butoxycarbonyl) glycine (10 g, 57.1 mmol) and methyl iodide (75 g, 528 mmol) in THF (600 mL) at 0 . The mixture was slowly allowed to warm to rt overnight. Water (300 mL) was added and extracted into ethyl acetate (2 x 500 mL). The aqueous layer was acidified to pH 3 with 1 M HCl extracted with ethyl acetate (2 x 500 mL). The combined organic layer was extracted with saturated aqueous sodium chloride (500 mL), dried (MgSO

Molecular Weight:189.21
XLogP3:0.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:189.10010796
Monoisotopic Mass:189.10010796
Topological Polar Surface Area:66.8
Heavy Atom Count:13
Complexity:207
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes