反应 #4517

ord-9c82aae6872744659c78caf24f2a0ad6

反应方程式

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
收率 196.4%

反应物

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

试剂

无

溶剂

ClCCl
methylene chloride

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    workup.WAITleft for an hour
  2. 2
    其他Evaporation of the solvent
  3. 3
    其他gave an oily residual which
  4. 4
    其他to give white solides
  5. 5
    过滤The solides were collected by filtration
  6. 6
    洗涤washed with water
  7. 7
    干燥dried over magnesium sulfate

实验过程

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).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US04725582uspto-grants-1988_02