Réaction #54605

Équation de réaction

L-Alanine

Boc-Ala-OSu

NMM

→

Boc-Ala-Ala-OH

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Autreevaporated to dryness
2. 2
   Autrethe oily residue re-evaporated twice with DMF (30 ml each)
3. 3
   AutreThe salt obtained
4. 4
   workup.ADDITIONadded, for 20 hours
5. 5
   AutreThe solvent was removed
6. 6
   ExtractionThe product was extracted into EtOAc (4 times 100 ml)
7. 7
   Lavagewashed twice with a small volume of H2O
8. 8
   Séchagedried over Na2SO4
9. 9
   Autreevaporated to a small volume
10. 10
    workup.ADDITIONtreated with petroleum ether until cloudiness
11. 11
    AutreA crystalline product formed on storage in the refrigerator overnight
12. 12
    AutreYield

Mode opératoire

L-Alanine (3.57 g, 40 mmol) was dissolved in 18.8 ml of Triton B (40 mmol), evaporated to dryness, and the oily residue re-evaporated twice with DMF (30 ml each). The salt obtained was stirred with 11.45 g of Boc-Ala-OSu (40 mmol) in 40 ml DMF, with 4 ml of NMM added, for 20 hours. The solvent was removed and the residue taken up in 10% HOAc (100 ml). The product was extracted into EtOAc (4 times 100 ml), washed twice with a small volume of H2O, dried over Na2SO4, evaporated to a small volume, and treated with petroleum ether until cloudiness developed. A crystalline product formed on storage in the refrigerator overnight: Yield, 8.2 g (76.3%); mp 115°-118°.

Source