Boc-D-Phenylglycine

White powder

(1) A mixture of (R)-2-amino-2-phenylacetic acid (200 g, 1.32 mol), potassium carbonate (218 g, 1.58 mol) was dissolved in water (2.0 L) and methanol (0.5 L), cooling to T <10 deg. C, di-tert-butyl dicarbonate (288 g, 1.32 mol) was added dropwise, room temperature reaction overnight, pH 4 to 5 with 1 N HCl, extraction with ethyl acetate (1.0 L * 3), was washed with saturated brine (1.0 L * 1), concentrated to give 315 g of a white solid, yield 95percent.The raw material 2 was dissolved in 10 ml of methanol, Then slowly add 20 ml of 1 N NaOH aqueous solutionAnd (Boc) 2O (2.18 g, 10 mmol).After 2 hours of reaction at room temperature, The pH was adjusted to 4-5 with 1N HCl solution.Followed by extraction with chloroform (3 x 30 ml) and the combined organic phases were dried over anhydrous magnesium sulfate to give the crude product. The crude product was purified by silica gel column chromatography, CH2Cl2 / MeOH (10: 1) as the mobile phase to afford intermediate 3 (955 mg, 76percent), Phenylglycine (1.51 g, 10 mmol) was dissolved in a mixture of dioxane and water (2:1, 30 mL) and 1.0 N aqueous sodium hydroxide, and the resulting mixture was cooledto 0°C. Di-tert-butyl dicarbonate (3.27 g, 15 mmol) and sodium hydrogen carbonate (0.84 g, 10 mmol) were added in one portion and the mixture was stirred at 0°C for 10 minutes. The ice bath was removed and the reaction mixture was stirred at ambient temperature for 24 hours. After this time, the reaction mixture was concentrated under reduced pressure and partitioned between ethyl acetate and water. The aqueous layer was acidified with 1.0N aqueous potassium hydrogen sulphate solution (pH 2.5) and subsequently washed with ethyl acetate (2 x 40 mL). The combined organic fractions were dried over magnesium sulfate and the solvent was removed in vacuo to yield the title compound (1.8 g, 72percent) as a clear oil, which solidified on standing. 1H NMR (400 MHz, CDC13): ö 8.08 (s, 1 H), 7.47-7.27 (m, 5 H), 5.48* OT+ (dd, J = 72.0 Hz, 6.5 Hz, 1 H), 5.13*0T+ (d, J = 5.6 Hz, 1 H), 3.71 (s, 1 H), 1.43 (s, 3 H), 1.21 (s, 6 H). * and refer to different isomers.Intermediate 4. (R)-2-((tert-butoxycarbonyl)amino)-2-phenylacetic acid (I4) General procedure: L-Phenylalanine (1.0 g, 6.05 mmol) and sodium carbonate (0.71 g, 6.70 mmol) in water (10 mL) was reacted with a solution of 2 (1.89 g, 6.36 mmol) in acetone (10 mL). The reaction mixture was stirred at room temperature till the reaction completes, as monitored by TLC. The resulting solution was concentrated, to the residue was added water (10 mL) and ethyl acetate (10 mL), pH adjusted to 6.0 with 10percent KHSO

Molecular Weight:251.28
XLogP3:2.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:251.11575802
Monoisotopic Mass:251.11575802
Topological Polar Surface Area:75.6
Heavy Atom Count:18
Complexity:303
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes