反応 #1558277

反応方程式

methyl chloroformate

(S)-2-amino-2-(tetrahydro-2H-pyran-4-yl)acetic acid

sodium carbonate

→

(S)-2-(Methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetic acid

溶媒

water

反応条件

後処理

1. 1
   その他thaw to ambient temperature
2. 2
   その他The reaction mixture was then partitioned between 1N HCl and ethyl acetate
3. 3
   その他The organic layer was removed
4. 4
   抽出the aqueous layer was further extracted with 2 additional portions of ethyl acetate
5. 5
   洗浄The combined organic layers were washed with brine
6. 6
   乾燥dried over magnesium sulfate
7. 7
   ろ過filtered
8. 8
   濃縮concentrated in vacuo
9. 9
   その他to afford Cap-170 a colorless residue

実験手順

To (S)-2-amino-2-(tetrahydro-2H-pyran-4-yl)acetic acid (505 mg; 3.18 mmol; obtained from Astatech) in water (15 ml) was added sodium carbonate (673 mg; 6.35 mmol), and the resultant mixture was cooled to 0° C. and then methyl chloroformate (0.26 ml; 3.33 mmol) was added dropwise over 5 minutes. The reaction was allowed to stir for 18 hours while allowing the bath to thaw to ambient temperature. The reaction mixture was then partitioned between 1N HCl and ethyl acetate. The organic layer was removed and the aqueous layer was further extracted with 2 additional portions of ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to afford Cap-170 a colorless residue. 1H NMR (500 MHz, DMSO-d6) δ ppm 12.65 (1 H, br s), 7.44 (1 H, d, J=8.24 Hz), 3.77-3.95 (3 H, m), 3.54 (3 H, s), 3.11-3.26 (2 H, m), 1.82-1.95 (1 H, m), 1.41-1.55 (2 H, m), 1.21-1.39 (2 H, m); LC/MS: Anal. Calcd. for [M+H]+ C9H16NO5: 218.1; found 218.1.

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