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 h 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 was 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 silica gel (90 g) using a mixture of dichloromethane/ethanol/25% ammonia in water 100:10:0.7 as eluant. 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 was extracted with dichloromethane (3×)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. customthe solvent removed in vacuo
8. customThe residue was purified by flash chromatography on silica gel (90 g)
9. additiona mixture of dichloromethane/ethanol/25% ammonia in water 100:10:0.7 as eluant
10. customPure fractions were collected
11. customthe solvent evaporated in vacuo