Boc-D-Phenylglycine Chemical Properties

Melting point:

88-91 °C

alpha 

-142 º (c=1% in ethanol)

Boiling point:

407.2±38.0 °C(Predicted)

Density 

1.182±0.06 g/cm3(Predicted)

refractive index 

-140 ° (C=1, EtOH)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO, Methanol

form 

Crystalline Powder

pka

3.51±0.10(Predicted)

color 

White

optical activity

[α]20/D 141.0±5.0°, c = 1% in ethanol

Water Solubility 

Insoluble in water. Slightly soluble in DMSO and methanol.

BRN 

3033982

InChI

InChI=1S/C13H17NO4/c1-13(2,3)18-12(17)14(9-11(15)16)10-7-5-4-6-8-10/h4-8H,9H2,1-3H3,(H,15,16)

InChIKey

KIAPYAZGXJCKQL-UHFFFAOYSA-N

SMILES

C(O)(=O)CN(C(OC(C)(C)C)=O)C1=CC=CC=C1

CAS DataBase Reference

33125-05-2(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29242990

MSDS

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

Boc-D-Phenylglycine Usage And Synthesis

Chemical Properties

White powder

Uses

It is a reagent of choice for assignment of absolute configuration of chiral primary amines by 1H NMR, giving better results than Mosher's acid ((R)-(+)-?-Methoxy-?-(trifluoromethyl)-phenyl-acetic acid. αR)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]-benzeneacetic Acid is D-(+)-2-Phenylglycine with Boc protecting group. (αR)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]-benzeneacetic Acid is used as part of a catalyst combination to catalyze regioselective [4 + 2] cycloadditions of β-substituted cyclic enones and polyconjugated malononitriles. It can also be used to catalyze stereoselective preparation of polyfunctional nitrocyclohexene carboxaldehydes.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

(1) A mixture of (R)-2-amino-2-phenylacetic acid (200 g, 1.32 mol) and potassium carbonate (218 g, 1.58 mol) was dissolved in a solvent mixture of water (2.0 L) and methanol (0.5 L), and cooled to a temperature of less than 10°C. Di-tert-butyl dicarbonate (288 g, 1.32 mol) was added dropwise, and the reaction was stirred at room temperature after the addition. After the addition, the reaction was stirred at room temperature overnight. After completion of the reaction, the pH of the reaction solution was adjusted to 4-5 with 1 N hydrochloric acid, followed by extraction with ethyl acetate (1.0 L × 3). The organic phases were combined, washed with saturated saline (1.0 L × 1), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a white solid product (315 g) in 95% yield.

References

[1] Journal of Medicinal Chemistry, 2013, vol. 56, # 20, p. 8049 - 8065
[2] Journal of Medicinal Chemistry, 1991, vol. 34, # 3, p. 968 - 978
[3] Tetrahedron Letters, 1995, vol. 36, # 29, p. 5227 - 5230
[4] Patent: CN104592163, 2016, B. Location in patent: Paragraph 0041; 0042
[5] Patent: CN106748892, 2017, A. Location in patent: Paragraph 0051; 0053; 0054; 0055

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