BOC-PRO-PRO-OH
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BOC-PRO-PRO-OH
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CAS No:
15401-08-8
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Formula:
C15H24N2O5
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Chemical Name:
BOC-PRO-PRO-OH
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Synonyms:
N-T-BOC-PRO-PRO;BOC-PRO-PRO-OH;boc-pro-pro;N-(tert-butoxycarbonyl)-Pro-Pro;(S)-1-((S)-1-(tert-Butoxycarbonyl)pyrrolidine-2-carbonyl)pyrrolidine-2-carboxylic acid;(tert-Butoxycarbonyl)prolylproline;Boc-L-Prolyl-L-proline;N-(tert-Butoxycarbonyl)prolylproline
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CAS No:
BOC-PRO-PRO-OH Use and Manufacturing
General procedure: To a solution of 130 mg N-Boc-D-Pro-L-Glu(OMe)-OMe(0.28 mmol) in 3 cm3 MeOH was added 0.7 cm3 1 MNaOH and the resulting solution was stirred at room temperature2 h. The reaction mixture was concentrated underreduced pressure, and the resulting aqueous phase wasacidified to pH 1 with conc. HCl and extracted with CH2-Cl2 (3 9 7 cm3). The combined organic layers werewashed with brine and dried over Na2SO4, and the solventwas removed under reduced pressure to afford the titlecompound.To a solution of 12.48 g (40 mmol) of N-Boc-L-prolyl-L-proline 3 in 50 mL of dioxane we added 40 mL of a 6.25 N solution of hydrogen chloride in dioxane. The mixture was stirred for 2 h, and the product was precipitated by adding 250 mL of diethyl ether. The precipitate was filtered off, washed twice with diethyl ether, and dried under reduced pressure until constant weight. Yield 8.95 g (90%), mp 164-166C, [alpha]D20 = -146 (c = 2, H2O). IR spectrum, nu, cm-1: 1754, 1665 (C=O). 1H NMR spectrum (CD3OD), delta, ppm: 1.95-2.14 m (6H, CH2), 2.29-2.40 m and 2.52-2.62 m (1H each, CH2), 3.34-3.42 m and 3.42-3.50 m (1H each, CH2), 3.56-3.64 m and 3.73-3.80 m (1H each, CH2), 4.51 t (1H, J = 6.9 Hz, CH), 4.66 t (1H, J = 7.0 Hz, CH). 13C NMR spectrum (CD3OD), deltaC, ppm: 25.06, 25.82, 29.45, 30.03, 47.67, 48.14, 60.30, 60.52, 168.33, 174.60. Found, %: C 48.04; H 7.12; Cl 14.51; N 11.08. C10H17ClN2O3. Calculated, %: C 48.29; H 6.89; Cl 14.25; N 11.26.
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