(2S,4S)-1-(TERT-BUTOXYCARBONYL)-4-PHENOXY-2-PYRROLIDINECARBOXYLIC ACID Chemical Properties

Boiling point:

455.8±45.0 °C(Predicted)

Density 

1.235±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

3.66±0.40(Predicted)

Appearance

White to off-white Solid

optical activity

-11.2°(C=0.01g/mL, ETOH, 20°C, 589nm)

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

29339900

(2S,4S)-1-(TERT-BUTOXYCARBONYL)-4-PHENOXY-2-PYRROLIDINECARBOXYLIC ACID Usage And Synthesis

Chemical Properties

White powder

Synthesis

General procedure for the synthesis of (2S,4S)-BOC-4-phenoxypyrrolidine-2-carboxylic acid from methyl (2S,4S)-1-BOC-4-phenoxypyrrolidine-2-carboxylate: Step 2: Synthesis of (2S,4S)-1-tert-butoxycarbonyl-4-phenoxy-2-pyrrolidine carboxylic acid Methyl (2S,4S)-1-tert-butoxycarbonyl-4-phenoxy-2-pyrrolidinylcarboxylate (4.31 g, 16.5 mmol) was dissolved in THF (132 ml), followed by addition of 0.25N NaOH solution (132 ml, 33.0 mmol). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and the residue obtained was acidified with 1N HCl and subsequently extracted with chloroform. The organic phase was washed with saturated brine and dried over anhydrous sodium sulfate. After removing the solvent by distillation under reduced pressure, the crude product obtained was recrystallized with hexane-chloroform mixed solvent to give (2S,4S)-BOC-4-phenoxypyrrolidine-2-carboxylic acid (2.96 g, 58% yield) as a final white crystalline powder. 1H-NMR (DMSO-d6) δ: 1.36 (s, 9H), 2.16 (d, J = 13.2 Hz, 1H), 2.56 (m, 1H), 3.46 (m, 1H), 3.71 (dt, J = 12.0, 5.4 Hz, 1H), 4.26 (dt, J = 9.5, 7.1 Hz, 1H), 4.99 (m, 1H). 6.85 (m, 2H), 6.94 (t, J = 7.3 Hz, 1H), 7.28 (t, J = 7.3 Hz, 2H).

References

[1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 8, p. 2725 - 2746
[2] Patent: EP1346982, 2003, A1

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