تفاعل #1442503

معادلة التفاعل

Fmoc-Osu

Amino acid

4-(2-Aminoethoxy)-2-hydroxybenzoic acid, hydrochloride

acetone water

Sodium Carbonate

→

4-[(2-fluorenylmethyloxycarbonylamino)ethoxy]-2-hydroxybenzoic acid

المذيبات

acetone

ظروف التفاعل

المعالجة

1. 1
   تركيزThe reaction mixture was concentrated
2. 2
   workup.DISSOLUTIONthe residue was dissolved in water
3. 3
   استخلاصextracted with ether (2×50 mL)
4. 4
   درجة الحرارةThe aqueous layer was cooled in an ice bath
5. 5
   أخرىThe solid obtained
6. 6
   ترشيحwas filtered
7. 7
   غسيلwashed with water
8. 8
   أخرىdried under vacuo (3.22 g)

الإجراء التجريبي

The Amino acid (14) (1.864 g; 8 mmol) from Step 2 was dissolved in 1:1 acetone—water (50 mL) containing Sodium Carbonate (1.696 g; 16 mmol). To the solution was added Fmoc-Osu (2.696 g; 8 mmol) in acetone (25 mL) dropwise at room temperature. The solution was stirred at room temperature for 18 h. The reaction mixture was concentrated and the residue was dissolved in water and extracted with ether (2×50 mL). The aqueous layer was cooled in an ice bath and acidified with 6N HCl to pH 3. The solid obtained was filtered and washed with water and dried under vacuo (3.22 g). NMR (300 MHz, DMSO-d6) δ7.9 (d, 2H), 7.65-7.75 (m, 2H), 7.55 (t, 2H), 7.4 (t, 2H), 7.3 (t, 2H), 6.5 (m, 2H), 4.35 (d, 2H), 4.25 (t, 1H), 4.05 (t, 2H), 3.4 (t, 2H).

المصدر