Reaktion #4517

ord-9c82aae6872744659c78caf24f2a0ad6

Reaktionsgleichung

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
Ausbeute 196.4%

Edukte

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

Reagenzien

Keine

Lösungsmittel

ClCCl
methylene chloride

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.WAITleft for an hour
  2. 2
    SonstigeEvaporation of the solvent
  3. 3
    Sonstigegave an oily residual which
  4. 4
    Sonstigeto give white solides
  5. 5
    FiltrationThe solides were collected by filtration
  6. 6
    Waschenwashed with water
  7. 7
    Trocknendried over magnesium sulfate

Vorschrift

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).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04725582uspto-grants-1988_02