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With sodium carbonate; sodium hydroxide; In water; at 20℃; for 4.5h;Cooling with ice; |
Methyl chloroformate (0.65 mL, 8.39 mmol) was added dropwise over 5 min to a cooled (ice-water) mixture OfNa2CO3 (0.449 g, 4.23 mmol), NaOH (8.2 mL of 1M/H2O, 8.2 mmol) and (S)-2-ammo-3-hydroxy-3-methylbutanoic acid (1.04 g, 7.81 mmol). The reaction mixture was stirred for 45 min, and then the cooling bath was removed and stirring was continued for an additional 3.75 hr. The reaction mixture was washed with CH2Cl2, and the aqueous phase was cooled with ice- water bath and acidified with concentrated HCl to a pH region of 1-2. The volatile component was removed in vacuo and the residue was taken up in a 2:1 mixture of MeOH/CH2Cl2 (15 mL) and filtered, and the filterate was rotervaped to afford Cap-65 as a white semi-viscous foam (1.236 g). 1H NMR (DMSOd6, delta = 2.5 ppm, 400 MHz): delta 6.94 (d, J = 8.5, 0.9 H), 6.53 (br s, 0.1H), 3.89 (d, J = 8.8, IH), 2.94 (s, 3H)5 1.15 (s, 3H), 1.13 (s, 3H). |
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Methyl chloroformate (0.65 mL, 8.39 mmol) was added dropwise over 5 min to a cooled (ice-water) mixture of Na2C03 (0.449 g, 4.23 mmol), NaOH (8.2 mL of IM/H2O, 8.2 mmol) and (5)-<strong>[2280-27-5]2-amino-3-hydroxy-3-methylbutanoic acid</strong> (1.04 g, 7.81 mmol). The reaction mixture was stirred for 45 min, and then the cooling bath was removed and stirring was continued for an additional 3.75 hr. The reaction mixture was washed with CH2CI2, and the aqueous phase was cooled with ice-water bath and acidified with concentrated HC1 to a pH region of 1-2. The volatile component was removed in vacuo and the residue was taken up in a 2: 1 mixture of MeOH/CH2Cl2 (15 mL) and filtered, and the filterate was rotervaped to afford Cap-65 as a white semi-viscous foam (1.236 g). XH NMR (DMSO-d6, delta = 2.5 ppm, 400 MHz): delta 6.94 (d, J = 8.5, 0.9 H), 6.53 (br s, 0.1H), 3.89 (d, J = 8.8, 1H), 2.94 (s, 3H), 1.15 (s, 3H), 1.13 (s, 3H). |
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With sodium carbonate; sodium hydroxide; In water; at 20℃; for 4.5h;Cooling with ice/water; |
Methyl chloroformate (0.65 mL, 8.39 mmol) was added dropwise over 5 min to a cooled (ice-water) mixture of Na2C03 (0.449 g, 4.23 mmol), NaOH (8.2 mL of IM/H2O, 8.2 mmol) and <strong>[2280-27-5](S)-<strong>[2280-27-5]2-amino-3-hydroxy-3-methylbutanoic acid</strong></strong> (1.04 g, 7.81 mmol). The reaction mixture was stirred for 45 min, and then the cooling bath was removed and stirring was continued for an additional 3.75 hr. The reaction mixture was washed with CH2Cl2, and the aqueous phase was cooled with ice-water bath and acidified with concentrated HC1 to a pH region of 1-2. The volatile component was removed in vacuo and the residue was taken up in a 2: 1 mixture of MeOH/CH2Ci2 (15 mL) and filtered, and the filterate was rotervaped to afford Cap-65 as a white semi-viscous foam (1.236 g). 1H NMR (DMSO-d6, delta = 2.5 ppm, 400 MHz): delta 6.94 (d, J = 8.5, 0.9 H), 6.53 (br s, 0.1H), 3.89 (d, J = 8.8, 1H), 2.94 (s, 3H), 1.15 (s, 3H), 1.13 (s, 3H). |
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With water; sodium carbonate; sodium hydroxide; for 4.5h;Cooling with ice; |
Ca -65[00187] Methyl chloroformate (0.65 mL, 8.39 mmol) was added dropwise over 5 min to a cooled (ice-water) mixture of Na2C03 (0.449 g, 4.23 mmol), NaOH (8.2 mL of IM/H2O, 8.2 mmol) and (5)-<strong>[2280-27-5]2-amino-3-hydroxy-3-methylbutanoic acid</strong> (1.04 g, 7.81 mmol). The reaction mixture was stirred for 45 min, and then the cooling bath was removed and stirring was continued for an additional 3.75 hr. The reaction mixture was washed with (¾(¾, and the aqueous phase was cooled with ice-water bath and acidified with concentrated HC1 to a pH region of 1-2. The volatile component was removed in vacuo and the residue was taken up in a 2: 1 mixture of MeOH/CH2Ci2 (15 mL) and filtered, and the filterate was rotervaped to afford Cap-65 as a white semi-viscous foam (1.236 g). ¾ NMR (DMSO-d6, delta = 2.5 ppm, 400 MHz): delta 6.94 (d, J = 8.5, 0.9 H), 6.53 (br s, 0.1H), 3.89 (d, J = 8.8, 1H), 2.94 (s, 3H), 1.15 (s, 3H), 1.13 (s, 3H). |
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With sodium carbonate; In water; for 4.5h;Cooling with ice; |
Methyl chloroformate (0.65 mL, 8.39 mmol) was added dropwise over 5 min to a cooled (ice-water) mixture of Na2C03 (0.449 g, 4.23 mmol), NaOH (8.2 mL of IM/H2O, 8.2 mmol) and (5)-<strong>[2280-27-5]2-amino-3-hydroxy-3-methylbutanoic acid</strong> (1.04 g, 7.81 mmol). The reaction mixture was stirred for 45 min, and then the cooling bath was removed and stirring was continued for an additional 3.75 hr. The reaction mixture was washed with (¾(¾, and the aqueous phase was cooled with ice-water bath and acidified with concentrated HCl to a pH region of 1-2. The volatile component was removed in vacuo and the residue was taken up in a 2: 1 mixture of MeOH/CH2Ci2 (15 mL) and filtered, and the filterate was rotervaped to afford Cap-65 as a white semi-viscous foam (1.236 g). XH NMR (DMSO-d6, delta = 2.5 ppm, 400 MHz): delta 6.94 (d, J = 8.5, 0.9 H), 6.53 (br s, 0.1H), 3.89 (d, J = 8.8, 1H), 2.94 (s, 3H), 1.15 (s, 3H), 1.13 (s, 3H). |
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With sodium carbonate; sodium hydroxide; In water; for 4.5h; |
Cap- 65 Methyl chloroformate (0.65 niL, 8.39 mmol) was added dropwise over 5 min to a cooled (ice-water) mixture of Na2C03 (0.449 g, 4.23 mmol), NaOH (8.2 mL of IM/H2O, 8.2 mmol) and (5)-<strong>[2280-27-5]2-amino-3-hydroxy-3-methylbutanoic acid</strong> (1.04 g, 7.81 mmol). The reaction mixture was stirred for 45 min, and then the cooling bath was removed and stirring was continued for an additional 3.75 hr. The reaction mixture was washed with CH2CI2, and the aqueous phase was cooled with ice-water bath and acidified with concentrated HC1 to a pH region of 1-2. The volatile component was removed in vacuo and the residue was taken up in a 2: 1 mixture of MeOH/CH^C^(15 mL) and filtered, and the filterate was rotervaped to afford Cap-65 as a white semi-viscous foam (1.236 g). XH NMR (DMSO-d6, delta = 2.5 ppm, 400 MHz): delta 6.94 (d, J = 8.5, 0.9 H), 6.53 (br s, 0.1H), 3.89 (d, J = 8.8, 1H), 2.94 (s, 3H), 1.15 (s, 3H), 1.13 (s, 3H). |
1.236 g |
With water; sodium carbonate; sodium hydroxide; for 4.5h;Cooling with ice; |
Methyl chloroformate (0.65 mL, 8.39 mmol) was added dropwise over 5 min to a cooled (ice-water) mixture ofNa2CO3 (0.449 g, 4.23 mmol), NaOH (8.2 mL of 1M/H2O, 8.2 mmol) and <strong>[2280-27-5](S)-<strong>[2280-27-5]2-amino-3-hydroxy-3-methylbutanoic acid</strong></strong>(1.04 g, 7.81 mmol). The reaction mixture was stirred for 45 min, and then the cooling bath was removed and stirringwas continued for an additional 3.75 hr. The reaction mixture was washed with CH2Cl2, and the aqueous phase wascooled with ice-water bath and acidified with concentrated HCl to a pH region of 1-2. The volatile component was removedin vacuo and the residue was taken up in a 2:1 mixture of MeOH/CH2Cl2 (15 mL) and filtered, and the filterate wasrotervaped to afford Cap-65 as a white semi-viscous foam (1.236 g). 1H NMR (DMSO-d6, delta = 2.5 ppm, 400 MHz): delta 6.94(d, J = 8.5, 0.9 H), 6.53 (br s, 0.1H), 3.89 (d, J = 8.8, 1H), 2.94 (s, 3H), 1.15 (s, 3H), 1.13 (s, 3H). |
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Methyl chloroformate (0.65 mL, 8.39 mmol) was added dropwise over 5 min to a cooled (ice-water) mixture OfNa2CO3 (0.449 g, 4.23 mmol), NaOH (8.2 mL of 1M/H2O, 8.2 mmol) and (S><strong>[2280-27-5]2-amino-3-hydroxy-3-methylbutanoic acid</strong> (1.04 g, 7.81 mmol). The reaction mixture was stirred for 45 min, and then the cooling bath was removed and stirring was continued for an additional 3.75 hr. The reaction mixture was washed with CH2Cl2, and the aqueous phase was cooled with ice-water bath and acidified with concentrated HCl to a pH region of 1-2. The volatile component was removed in vacuo and the residue was taken up in a 2: 1 mixture of MeOH/CH2Cl2 <n="83"/>(15 mL) and filtered, and the filterate was rotervaped to afford Cap-65 as a white semi-viscous foam (1.236 g). 1H NMR (DMSO-d6, delta = 2.5 ppm, 400 MHz): delta 6.94 (d, J = 8.5, 0.9 H), 6.53 (br s, 0.1H), 3.89 (d, J = 8.8, IH), 2.94 (s, 3H), 1.15 (s, 3H), 1.13 (s, 3H). |
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Cap- 65Methyl chloroformate (0.65 mL, 8.39 mmol) was added dropwise over 5 min to a cooled (ice-water) mixture OfNa2CO3 (0.449 g, 4.23 mmol), NaOH (8.2 mL of 1M/H2O, 8.2 mmol) and (5*)-3-hydroxy-2-(methoxycarbonylamino)-3- methylbutanoic acid (1.04 g, 7.81 mmol). The reaction mixture was stirred for 45 min, and then the cooling bath was removed and stirring was continued for an additional 3.75 hr. The reaction mixture was washed with CH2Cl2, and the aqueous phase was cooled with ice-water bath and acidified with concentrated HCl to a pH region of 1-2. The volatile component was removed in vacuo and the residue was <n="78"/>taken up in a 2: 1 mixture of MeOH/CH2Cl2 (15 mL) and filtered, and the filterate was rotervaped to afford Cap-65 as a white semi-viscous foam (1.236 g). 1H NMR (DMSO-d6, delta = 2.5 ppm, 400 MHz): delta 6.94 (d, J = 8.5, 0.9 H), 6.53 (br s, 0.1H), 3.89 (d, J = 8.8, IH), 2.94 (s, 3H), 1.15 (s, 3H), 1.13 (s, 3H) |
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With sodium carbonate; sodium hydroxide; In water;Cooling; |
Methyl chloroformate (0.65 mL, 8.39 mmol) was added dropwise over 5 min to a cooled (ice-water) mixture of Na2CO3 (0.449 g, 4.23 mmol), NaOH (8.2 mL of 1M/H2O, 8.2 mmol) and <strong>[2280-27-5](S)-<strong>[2280-27-5]2-amino-3-hydroxy-3-methylbutanoic acid</strong></strong> (1.04 g, 7.81 mmol). The reaction mixture was stirred for 45 min, and then the cooling bath was removed and stirring was continued for an additional 3.75 hr. The reaction mixture was washed with CH2Cl2, and the aqueous phase was cooled with ice-water bath and acidified with concentrated HCl to a pH region of 1-2. The volatile component was removed in vacuo and the residue was taken up in a 2:1 mixture of MeOH/CH2Cl2 (15 mL) and filtered, and the filterate was rotervaped to afford Cap-65 as a white semi-viscous foam (1.236 g). 1H NMR (DMSO-d6, delta=2.5 ppm, 400 MHz): delta 6.94 (d, J=8.5, 0.9H), 6.53 (br s, 0.1H), 3.89 (d, J=8.8, 1H), 2.94 (s, 3H), 1.15 (s, 3H), 1.13 (s, 3H). |