(2S,3S,5S)-2-(2,6-Dimethylphenoxyacetyl)amino-3-hydroxy-5-(tert-butoxycarbonyl)amino-1,6-diphenylhexane

(2S,3S,5S)-2-(2,6-Dimethylphenoxyacetyl)amino-3-hydroxy-5-(tert-butoxycarbonyl)amino-1,6-diphenylhexane Property

Boiling point:

758.1±60.0 °C(Predicted)

Density 

1.133±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

soluble in Chloroform, Dichloromethane, Methanol

form 

Solid

pka

12.33±0.46(Predicted)

color 

White

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

(2S,3S,5S)-2-(2,6-Dimethylphenoxyacetyl)amino-3-hydroxy-5-(tert-butoxycarbonyl)amino-1,6-diphenylhexane Chemical Properties,Usage,Production

Chemical Properties

White Solid

Uses

(2S,3S,5S)-2-(2,6-Dimethylphenoxyacetyl)amino-3-hydroxy-5-(tert-butyloxycarbonylamino)-1,6-diphenylhexane (cas# 192725-45-4) is a compound useful in organic synthesis.

Synthesis

Example 18. Preparation of (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-(tert-butoxycarbonyl)amino-1,6-diphenylhexane: tert-butyl (1S,3S,4S)-1 -benzyl-4-amino-3- hydroxy-5-phenylpentylcarbamate (38.5 mg, 0.1 mmol), 2, 6-dimethylphenoxyacetic acid (18.9 mg, 1.05 eq.), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (29.7 mg, 1.5 eq.) and 1-hydroxybenzotriazole (20.4 mg, 1.5 eq.) were dissolved in N,N-dimethylformamide (1 mL) and stirred for 4 min. Subsequently, N-methylmorpholine (27.5 μL, 2.5 eq.) was added to the reaction mixture and stirring was continued for 16 hours. After completion of the reaction, the reaction was quenched with saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic phase was washed with 10% citric acid solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography (3% methanol/dichloromethane) afforded a white solid product (240 mg, 76.7% yield).1H NMR (300 MHz, DMSO-D6) δ ppm: 1.31 (s, 9H), 1.39-1.55 (m, 2H), 2.14 (s, 6H), 2.61 (d, J = 6.99 Hz, 2H), 2.80 (d, J = 7.35 Hz, 2H), 3.61-3.70 (m, 1H), 3.84 (m, 1H), 4.00-4.11 (m, 2H), 4.20-4.38 (m, 1H), 4.99 (d, 1H), 6.66 (d, J = 9.19 Hz, 1H), 6.88-7.28 (m, 13H), 7.43 (d, J = 9.19 Hz, 13H), 7.43 (d, J = 9.19 Hz, 13H), 7.43 (d, J = 9.19 Hz, 13H), 7.43 (d, J = 6.99 Hz, 13H) 7.43 (d, J = 9.56 Hz, 1H); MS m/z 547.4 (M + H)+.

References

[1] Patent: EP1170289, 2002, A2. Location in patent: Page 41
[2] Patent: WO2008/27932, 2008, A2. Location in patent: Page/Page column 101
[3] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 21, p. 3101 - 3103
[4] Letters in Organic Chemistry, 2018, vol. 15, # 2, p. 87 - 91