1670
H.-K. Kim, K.-J.J. Park / Tetrahedron Letters 53 (2012) 1668–1670
Trenner, N. R.; Peck, R. L.; Buhs, R. P.; Howe, E.; Putter, I.; Hunnewell, B. D.;
0 °C. The mixture was stirred at 0 °C for 4 h and concentrated under reduced
pressure. Et3N (1.16 mL, 8.37 mmol) and CH2Cl2 (30 mL) was added to the
mixture and stirred at 0 °C for 10 min. Methanesulfonyl chloride (0.73 g,
6.14 mmol) was added next, and the mixture was stirred at 0 °C for 1 h. DBU
(1.27 g, 8.37 mmol) was added to the mixture at 0 °C and stirred at room
temperature for 2 d. After NaOH (1.12 g, 27 mmol) in water (20 mL) and MeOH
(20 mL) were added, the mixture was stirred at room temperature for 4 h. 50 mL
of ethanol/isopropyl alcohol was added. The precipitate salts were filtered, and
the filtrated was cooled to 0 °C in the ice bath. Glacial acetic acid was added
dropwise to the well-stirred mixture to reach pH 6.0 and gave a colorless solid.
The crystalline precipitate was filtered and washed twice with 1:1 ethanol/
Ormond, R.; Downing, G.; Lyons, J. E.; Newstead, E.; Chaiet, L.; Folkers, K. J. Am.
Chem. Soc. 1955, 77, 2344–2345; (c) Shoji, J. J. Antibiotics 1956, 9, 164–167; (d)
Gordeev, M. F.; Luehr, G. W.; Hui, H. C.; Gordon, E. M.; Patel, D. V. Tetrahedron
1998, 54, 15879–15890.
2. (a) Chain, E. B. Annu. Rev. Biochem. 1958, 27, 167–222; (b) David, S. J. Antimicrob.
Chemother. 2001, 47, 203–206; (c) Li, X. M.; Meng, X.; Duan, H. D.; Wang, L. Z.;
Wang, S. X.; Zhang, Y.; Qin, D. W. Arch. Pharm. 2010, 343, 473–475; (d) Deamici,
M.; Demicheli, C.; Cateni, F.; Carrea, G.; Ottolina, G. Tetrahedron: Asymmetry
1993, 4, 1073–1080.
3. (a) Hofmann, S. G.; Pollack, M. H.; Otto, M. W. CNS Drug Rev. 2006, 12, 208–217;
(b) Norberg, M. M.; Krystal, J. H.; Tolin, D. F. Biol. Psychiatry 2008, 63, 1118–
1126; (c) Ressler, K. J.; Rothbaum, B. O.; Tannenbaum, L.; Anderson, P.; Graap, K.;
Zimand, E.; Hodges, L.; Davis, M. Arch. Gen. Psychiatry. 2004, 61, 1136–1144; (d)
Guastella, A. J.; Richardson, R.; Lovibond, P. F.; Rapee, R. M.; Gaston, J. E.;
Mitchell, P.; Dadds, M. R. Biol. Psychiatry 2008, 63, 544–549.
isopropyl alcohol and diethyl ether to give
D-4-amino-3-isoxazolidinone
(315 mg, 55%). mp 146–148 °C; ½a D25
ꢀ
+110 (c 1.0, H2O); 1H NMR (DMSO-d6,
300 MHz) d 4.38 (t, 1H), 3.51 (m, 2H); 13C NMR (DMSO-d6, 75 MHz) d 174.5,
75.1, 53.6; HRMS (ESI) m/z (M+H)+ calcd for C3H6N2O2 = 102.0919, found
102.0743.
4. (a) Gottlieb, J. D.; Cather, C.; Shanahan, M.; Creedon, T.; Macklin, E. A.; Goff, D. C.
Schizophr. Res. 2011, 131, 69–74; (b) Goff, D. C.; Cather, C.; Gottlieb, J. D.; Evins,
A. E.; Walsh, J.; Raeke, L.; Otto, M. W.; Schoenfeld, D.; Green, M. F. Schizophr. Res.
2008, 106, 320–327.
5. (a) Stammer, C. H.; Wilson, A. N.; Holly, F. W.; Folkers, K. J. Am. Chem. Soc. 1955,
77, 2346–2347; (b) Stammer, C. H.; Wilson, A. N.; Spencer, C. F.; Bachelor, F. W.;
Holly, F. W.; Folkers, K. J. Am. Chem. Soc. 1957, 79, 3236–3240; Plattner, Pl. A.;
Boller, A.; Frick, H.; Furst, A.; Hegedus, B.; Kirchensteiner, H.; Majnoni, St.;
Schlapfer, R.; Spiegelberg, H.; Hoffmann-La Roche, A.-G.; Basel, S. Helv. Chim.
Acta 1957, 40, 1531–1552.
(d) Synthesis of compound 7: Diethyl azodicarboxylate (1.26 g, 7.26 mmol) was
added to the solution, consisting of compound
3 (1.2 g, 5.58 mmol),
triphenylphosphine (1.90 g, 7.26 mmol), and N-hydroxyphthalimide (1.18 g,
7.26 mol) in THF (100 ml) at 0 °C. Being stirred at room temperature for 2 h,
the mixture was concentrated under reduced pressure. To the residue was
added water (80 ml), and the mixture was extracted with diethyl ether
(2 ꢂ 100 ml). The organic layer was dried over MgSO4 and evaporated. The
crude residue was purified by flash chromatography on silica gel
(eluent:AcOEt/Hexane, 1:4) to give compound
7
(1.7 g, 87%) as an oil. 1H
NMR (CDCl3, 300 MHz) d 7.76–7.79(m, 2H), 7.69–7.73(m, 2H), 5.9 (m, 1H), 4.71
(dd, J = 10.6, 3.0 Hz, 1 H), 4.53 (m, 1H), 4.35 (m, 1H), 4.12 (dd, J = 9.2, 3.4 Hz, 1
H), 3.65 (s, 3H); 13C NMR (CDCl3,75 MHz) d 170.0, 163.3, 156.0, 134.8, 128.7,
127.9. 123.8, 115.8, 80.4, 71.3, 53.1, 52.8, 14.5; HRMS (ESI) m/z (M+H)+ calcd
for C17H19N2O7 = 360.2421, found 360.3474.
6. Hulme, A. N.; Montgomery, C. H.; Henderson, D. K. J. Chem. Soc. Perk Trans. 1
2000, 1837–1841.
7. Nagle, A. S.; Salvatore, R. N.; Chong, B.-D.; Jung, K. W. Tetrahedron 2000, 41,
3011–3014.
8. Procedures and selected data
(e) Synthesis of compound 6 from compound 7: Hydrazine (0.173 mL,
(a) Synthesis of compound 2: Acetyl chloride (4.06 mL, 57.14 mmol) was added to
4.17 mmol) was added to a solution of compound 7 (0.5 g, 1.39 mmol) in
MeOH (20 mL) and CH2Cl2 (20 mL) and stirred at room temperature for 3 h.
Aqueous 5% NaHCO3 was added to neutralize the reaction mixture, and the
mixture was concentrated under reduced pressure. The crude residue was
dissolved in MeOH (20 mL) and CH2Cl2 (20 mL), and KCN (18 mg, 0.28 mmol)
was added to the reaction mixture. The mixture was stirred at room
temperature for 4 h, followed by the addition of NaOH (0.39 g, 9.72 mmol) in
water (20 mL) and MeOH (20 mL). The mixture was stirred at room
temperature for 4 h. After 50 mL of ethanol/isopropyl alcohol was added, the
precipitate salts were filtered, and the filtrated was cooled to 0 °C in the ice
bath. Glacial acetic acid was added dropwise to the well-stirred mixture to
reach pH 6.0 and gave a colorless solid. The crystalline precipitate was filtered
and washed twice with 1:1 ethanol/isopropyl alcohol and diethyl ether to give
MeOH (100 mL) cooled in ice. The solution was stirred for 5 min.
D-Serine (2 g,
19.04 ml) was added in one portion to a solution of -serine in MeOH, and the
D
solution was heated to reflux. The mixture was stirred for 2 h at reflux and
cooled to room temperature. The reaction was evaporated under reduced
pressure and gave a colorless solid. The solid was filtered and washed with
CH2Cl2 (100 ml) to give D-serine methyl ester hydrochloride 2 (2.86 g, 97%) as a
white solid. mp 164–166 °C; ½a D20
ꢀ
ꢁ4 (c = 4.0, EtOH); 1H NMR (CD3OD, 300 MHz)
d
4.03 (m, 1H), 3.90 (dd, J = 6.6 Hz, J = 18.6 Hz, 1H), 3.82 (dd, J = 4.8 Hz,
J = 17.4 Hz, 1H), 3.81 (s, 3H); 13C NMR (DMSO-d6, 75 MHz) d 168.5, 59.5, 54.4,
52.8; HRMS (ESI) m/z (M+H)+ calculated for C4H10ClNO3 = 155.5801, found
155.4573.
(b) Synthesis of compound 3: Et3N (2.25 mL, 16.23 mmol) was added to a solution
of serine methyl ester hydrochloride (1 g, 6.45 mmol) in MeOH (20 ml) and
ethyl trifluoroacetate (1.54 mL, 12.90 mmol) was added. After the mixture was
stirred for 15 h at room temperature, it was concentrated under reduced
pressure. The residue was purified by flash chromatography on silica gel
(eluent:AcOEt/Hexane, 1:1) to give compound 3 (1.36 g, 98%) as a colorless oil.
D
-4-amino-3-isoxazolidinone (121 mg, 85%).
(f) Synthesis of compound from compound 10: Sodium methoxide
(5.477 mmol) in MeOH was added to solution of hydroxylamine
6
a
hydrochloride (127 mg, 1.83 mmol) in MeOH (10 mL) and stirred at room
temperature for 30 min. The mixture was cooled to 0 °C, and sodium chloride
was filtered. A solution of compound 10 (320 mg, 1.12 mmol) in H2O (10 mL)
was added to the filtrate at 0 °C. The mixture was stirred at 0 °C for 5 h and
stirred at room temperature for 4 h. 40 mL of ethanol/isopropy alcohol was
added. The precipitate salts were filtered, and the filtrated was cooled to 0 °C
in the ice bath. Glacial acetic acid was added dropwise to the well-stirred
½
a 2D0
ꢀ
ꢁ34.7 (c = 4.4, MeOH); 1H NMR (CDCl3, 300 MHz) d 7.52 (s, 1H), 4.45–4.56
(m, 1H), 3.95 (dd, J = 6.8 Hz, J = 18.8 Hz, 1H), 3.89 (dd, J = 5.2 Hz, J = 17.8 Hz, 1H),
3.77 (s, 3H); 13C NMR (CDCl3, 75 MHz) d 171.4, 156.1, 115.5, 62.6, 55.5, 52.2;
HRMS (ESI) m/z (M+H)+ calcd for C6H8F3NO4 = 215.1272, found 215.1354.
(c) Synthesis of compound 6 from compound 3: Sodium methoxide (12.27 mmol)
in MeOH was added to a solution of hydroxylamine hydrochloride (465 mg,
6.69 mmol) in MeOH (10 mL). The mixture was stirred at room temperature for
30 min and cooled to 0 °C. Then the sodium chloride was filtered. A solution of
compound 3 (1.2 g, 5.58 mmol) in CH3CN (20 mL) was added to the filtrate at
mixture to reach pH 6.0 and yielded
precipitate was filtered and washed twice with 1:1 ethanol/isopropyl alcohol
and diethyl ether to give -4-amino-3-isoxazolidinone (55 mg, 48%).
a colorless solid. The crystalline
D