Aniline → HCID 131713947, compound

Temperature

0 °C

(S)-P-[3-[[(Phenylmethoxy)carbonyl]amino]-2-oxo-1-azetidinyl]-N-propylphosphonamidic acid, methyl ester, potassium salt (3.0 g) was dissolved in distilled dichloromethane (30 ml) and cooled to 0°-5° C. in an ice-bath under a nitrogen atmosphere. Bis(trimethylsilyl)acetamide (6.88 g) was added and the mixture stirred at 0° C. for 0.5 hour. Trimethylsilylbromide (3.9 g) was added and the mixture stirred for 3 hours at 0° to 5° C. The solvent and excess bis(trimethylsilyl)acetamide and trimethylsilylbromide were removed in vacuo. The oil was taken up in three 20 ml portions of dry toluene and the toluene was removed in vacuo yielding a pale residue. The residue was dissolved in dry tetrahydrofuran (50 ml) and 2 equivalents of distilled aniline (1.57 g) in absolute ethanol (15 ml) was added; the mixture was stirred at room temperature for 0.5 hour. The solvents were removed in vacuo yielding an oily residue which was dissolved in acetonitrile (100 ml) by heating to 80° C. The hot acetonitrile solution was filtered and stored in the freezer overnight (-10° C.). The title compound crystallized yielding 2.65 g of material, melting point 186°-190° C., dec.

1. temperaturecooled to 0°-5° C. in an ice-bath under a nitrogen atmosphere
2. stirringthe mixture stirred for 3 hours at 0° to 5° C
3. customThe solvent and excess bis(trimethylsilyl)acetamide and trimethylsilylbromide were removed in vacuo
4. customthe toluene was removed in vacuo
5. customyielding a pale residue
6. stirringthe mixture was stirred at room temperature for 0.5 hour
7. customThe solvents were removed in vacuo
8. customyielding an oily residue which
9. temperatureby heating to 80° C
10. filtrationThe hot acetonitrile solution was filtered
11. customstored in the freezer overnight (-10° C.)
12. customThe title compound crystallized

ORD record

ord-3b2f26c8a85248378252654e6a25811b

Source dataset

uspto-grants-1984_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04478749