تفاعل #1747882

معادلة التفاعل

13

(3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-(triisopropyl-silanyloxy)hexanoic Acid Methyl Ester

NaOH

→

acid 14

(3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-(triisopropyl-silanyloxy)hexanoic Acid

المذيبات

THF MeOH

ظروف التفاعل

المعالجة

1. 1
   أخرىovernight
2. 2
   أخرىat rt
3. 3
   تركيزThe reaction mixture was concentrated
4. 4
   workup.ADDITIONdiluted with H2O (20 mL)
5. 5
   درجة الحرارةcooled to 0° C.
6. 6
   استخلاصextracted with EtOAc (3×20 mL)
7. 7
   غسيلThe combined organic layers were washed with NaCl (50 mL, sat)
8. 8
   تجفيفdried (Na2SO4)
9. 9
   ترشيحfiltered
10. 10
    أخرىevaporated

الإجراء التجريبي

To a solution of 13 (2.2 g, 4.7 mmol) in 50 mL of THF/MeOH (1:1), cooled to 0° C., 1N NaOH solution (55 mL, 32 mmol) was added. The reaction was stirred at 0° C. for 2 h and then overnight at rt. The reaction mixture was concentrated and diluted with H2O (20 mL), cooled to 0° C., acidified to pH 2 with 1N KHSO4 solution and extracted with EtOAc (3×20 mL). The combined organic layers were washed with NaCl (50 mL, sat), dried (Na2SO4), filtered and evaporated. The resulting acid 14 was obtained as a colorless oil (1.76 g, 86%) and used directly in the next step. 1H-NMR (500 MHz, CDCl3): 0.86 (m, 3H), 0.95 (d, J=6.7 Hz, 3H), 1.04-1.14 (m, 21H), 1.90-2.00 (m, 1H), 2.52-2.72 (m, 2H), 3.60-3.62 (m, 1H), 4.28-4.36 (m, 1H), 5.02 (d, J=10.4 Hz, 1H), 5.07-5.13 (m, 3H), 7.25-7.35 (m, 5H).

المصدر