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

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

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

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

(2S,3S,5S)-2-(2,6-Dimethylphenoxyacetyl)amino-3-hydroxy-5-(tert-butoxycarbonyl)amino-1,6-diphenylhexane(192725-45-4)Related Product Information

• (2S)-(1-Tetrahydropyramid-2-one)-3-methylbutanoic acid
• 2,6-Dimethylphenoxyacetic acid
• N-[(1S,2S,4S)-4-amino-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-2-(2,6-dimethylphenoxy)acetamide