BOC-L-Phenylglycinol Chemical Properties

Melting point:

136-139 °C(lit.)

alpha 

+37°(19℃, c=1, CHCl3)

Boiling point:

382.4±35.0 °C(Predicted)

Density 

1.101±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

11.55±0.46(Predicted)

color 

White to Orange to Green

optical activity

[α]19/D +37°, c = 1 in chloroform

Water Solubility 

Insoluble in water.

BRN 

4316842

InChIKey

IBDIOGYTZBKRGI-LLVKDONJSA-N

CAS DataBase Reference

117049-14-6(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29051990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

BOC-L-Phenylglycinol Usage And Synthesis

Chemical Properties

White solid

Uses

N-Boc-L-alpha-phenylglycinol is an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dye fields. Phenylglycinol-derived oxazolopiperidone lactams is used as starting materials for the enantioselective synthesis of piperidine-containing alkaloids.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

GENERAL STEPS: Di-tert-butyl dicarbonate (31.82 g, 146.8 mmol) was slowly added to a solution of anhydrous tetrahydrofuran (292 mL) containing (R)-(-)-2-phenylglycinol (20.00 g, 145.8 mmol) and triethylamine (24.4 mL, 175.0 mmol) at 0 °C. The reaction mixture was stirred continuously for 3 hours at 0 °C. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure by rotary evaporator. The concentrated residue was dissolved in dichloromethane (200 mL) and washed with 1N hydrochloric acid (240 mL). The aqueous layer was back-extracted with dichloromethane (2 x 100 mL). All organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated again by rotary evaporator under reduced pressure to give a white solid product ((R)-tert-butyl 2-hydroxy-1-phenylethyl)carbamate (34.59 g, yield >99%). The product was characterized by 1H NMR (CDCl3): δ 1.43 (s, 9H), 2.29 (br s, 1H), 3.84-3.87 (m, 2H), 4.79 (br s, 1H), 7.29-7.39 (m, 5H).

References

[1] Tetrahedron Asymmetry, 2007, vol. 18, # 23, p. 2758 - 2767
[2] Patent: WO2007/22371, 2007, A2. Location in patent: Page/Page column 28
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 20, p. 8049 - 8065
[4] Comptes Rendus Chimie, 2010, vol. 13, # 5, p. 544 - 547
[5] Letters in Organic Chemistry, 2011, vol. 8, # 1, p. 38 - 42

BOC-L-Phenylglycinol(117049-14-6)Related Product Information

• Amlodipine Besylate
• (S)-(+)-2-Phenylglycinol
• tert-Butyl acetate
• DL-2-Phenylglycinol
• tert-Butanol
• tert-Butyl peroxyacetate
• (S)-Amlodipine
• Diethylene glycol dibenzoate
• 4,4'-Diaminodiphenylsulfone
• Trimethoprim
• Ketorolac tromethamine
• Fosfomycin tromethamine
• Triamterene
• 2-AMINO-1-PHENYLETHANOL
• Hydrogenated Cottonseed Oil
• (S)-N-BOC-4-FLUOROPHENYLGLYCINE
• (2R,3S)-Boc-3-Phenylisoserine
• BOC-PHG-OSU