تفاعل #4517

ord-9c82aae6872744659c78caf24f2a0ad6

معادلة التفاعل

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
المردود 196.4%

المتفاعلات

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

الكواشف

لا شيء

المذيبات

ClCCl
methylene chloride

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.WAITleft for an hour
  2. 2
    أخرىEvaporation of the solvent
  3. 3
    أخرىgave an oily residual which
  4. 4
    أخرىto give white solides
  5. 5
    ترشيحThe solides were collected by filtration
  6. 6
    غسيلwashed with water
  7. 7
    تجفيفdried over magnesium sulfate

الإجراء التجريبي

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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US04725582uspto-grants-1988_02