Реакция #4517

ord-9c82aae6872744659c78caf24f2a0ad6

Уравнение реакции

O
water
COC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)OC(C)(C)C
L-Ala-D-Glu(OH)OBzl
COC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)OC(C)(C)C
Boc-L-Ala-D-Glu(OH)OMe
C[Si](C)(C)C(C(N)=O)[Si](C)(C)C
bis(trimethylsilyl)acetamide
CCCCCCCCCCCCCCCCCC(=O)Cl
stearoyl chloride
→
CCCCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)O)C(=O)OCc1ccccc1
stearoyl-L-Ala-D-Glu(OH)OBzl
Выход 196.4%

Реактанты

O
water
COC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)OC(C)(C)C
L-Ala-D-Glu(OH)OBzl
COC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)OC(C)(C)C
Boc-L-Ala-D-Glu(OH)OMe
C[Si](C)(C)C(C(N)=O)[Si](C)(C)C
bis(trimethylsilyl)acetamide
CCCCCCCCCCCCCCCCCC(=O)Cl
stearoyl chloride

Реагенты

Нет

Растворители

ClCCl
methylene chloride

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    workup.WAITleft for an hour
  2. 2
    ДругоеEvaporation of the solvent
  3. 3
    Другоеgave an oily residual which
  4. 4
    Другоеto give white solides
  5. 5
    ФильтрацияThe solides were collected by filtration
  6. 6
    Промывкаwashed with water
  7. 7
    Сушкаdried over magnesium sulfate

Методика

L-Ala-D-Glu(OH)OBzl (1) (942 mg) was suspended in methylene chloride (40 ml), and bis(trimethylsilyl)acetamide (1.20 g) was added to the suspension under stirring. The resulting solution was treated with stearoyl chloride (900 mg) at ambient temperature and left for an hour. Evaporation of the solvent gave an oily residual which was treated with water to give white solides. The solides were collected by filtration, washed with water and dried over magnesium sulfate to give stearoyl-L-Ala-D-Glu(OH)OBzl (2) (1.60 g).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US04725582uspto-grants-1988_02