反应详情

The above 2-amino-7-((2,2,2-trichloro-ethoxycarbonylamino)methyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (4.0 g, 8.0 mmol) was dissolved in a mixture of tetrahydrofuran (15 ml) and a aqueous phosphate buffer (pH 3; 5 ml) followed by addition of zinc (16 g, 0.244 mol). The reaction mixture was stirred for 6 hours at room temperature at which time the solvent was removed in vacuo. To the residue was added diethyl ether (20 ml) and water (40 ml). Sodium carbonate was added to the aqueous phase until pH=8 and the aqueous phase extracted with dichloromethane (3×). The combined organic phases were dried (MgSO4), filtered and the solvent removed in vacuo. The residue was purified by flash chromatography on sillicagel (90 g) using a mixture of dichloromethane/ethanol/25% ammonia in water 100:10:0.7 as eluent. Pure fractions were collected and the solvent evaporated in vacuo affording 1.52 g (61%) of 2-amino-7-aminomethyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester.

1. customwas removed in vacuo
2. additionTo the residue was added diethyl ether (20 ml) and water (40 ml)
3. additionSodium carbonate was added to the aqueous phase until pH=8
4. extractionthe aqueous phase extracted with dichloromethane (3×)
5. dry with materialThe combined organic phases were dried (MgSO4)
6. filtrationfiltered
7. customthe solvent removed in vacuo
8. customThe residue was purified by flash chromatography on sillicagel (90 g)
9. additiona mixture of dichloromethane/ethanol/25% ammonia in water 100:10:0.7 as eluent
10. customPure fractions were collected
11. customthe solvent evaporated in vacuo