Triethylamine → N-t-butoxycarbonyl-p-hydroxymethylphenylglycine

To a solution of p-hydroxymethylphenylglycine (8.0 g, 0.044 mole) and triethylamine (8.8 g., 0.087 mole) in 160 ml water was added t-butoxycarbonyl azide (6.95 g., 0.049 mole) dissolved in 120 ml tetrahydrofuran. After stirring overnight at room temperature, the reaction mixture was washed twice with 200 ml. portions of ether. The aqueous layer was covered with ether and in an ice bath was acidified to pH 3-3.5 with 3N hydrochloric acid. The acidic solution was extracted three times with 200 ml portions of ether. The combined ether layers were washed with saturated sodium chloride solution, dried, and the ether evaporated under reduced pressure. The resulting oil was triturated with chloroform-hexane and the solid filtered off to give N-t-butoxycarbonyl-p-hydroxymethylphenylglycine (7.74 g, 63 percent yield), m.p. 139°-141.5° (dec.).

1. washthe reaction mixture was washed twice with 200 ml
2. customThe aqueous layer was covered with ether and in an ice bath
3. extractionThe acidic solution was extracted three times with 200 ml portions of ether
4. washThe combined ether layers were washed with saturated sodium chloride solution
5. customdried
6. customthe ether evaporated under reduced pressure
7. customThe resulting oil was triturated with chloroform-hexane
8. filtrationthe solid filtered off

ORD-Eintrag

ord-012d61a002d940c3a5eef9737d53a4cd

Quelldatensatz

uspto-grants-1976_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US03972919