Reacción #1115011

Ecuación de reacción

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

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothaw to ambient temperature
2. 2
   OtroThe reaction mixture was then partitioned between 1N HCl and ethyl acetate
3. 3
   OtroThe organic layer was removed
4. 4
   Extracciónthe aqueous layer was further extracted with 2 additional portions of ethyl acetate
5. 5
   LavadoThe combined organic layers were washed with brine
6. 6
   Secadodried over magnesium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   Otroto afford Cap-170 a colorless residue

Procedimiento

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.

Fuente