L-Alanine → N-((1,1-Dimethylethoxy)carbonyl)-L-alanyl-L-alanine

HRID 26327

Reaction equation

HRID 26327 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].[NH:7]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@H:8]([C:10](ON1C(=O)CCC1=O)=[O:11])[CH3:9].CN1CCOCC1>CN(C=O)C>[NH:7]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[C@H:8]([C:10]([NH:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3])=[O:11])[CH3:9]

Participants

5

Reactant 3

HCID 5950L-AlanineHCID 79724-MethylmorpholineHCID 11011585Boc-Ala-OSu

Product 1

HCID 6992569N-((1,1-Dimethylethoxy)carbonyl)-L-alanyl-L-alanine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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°.

Workup

  1. customevaporated to dryness
  2. customthe oily residue re-evaporated twice with DMF (30 ml each)
  3. customThe salt obtained
  4. additionadded, for 20 hours
  5. customThe solvent was removed
  6. extractionThe product was extracted into EtOAc (4 times 100 ml)
  7. washwashed twice with a small volume of H2O
  8. dry with materialdried over Na2SO4
  9. customevaporated to a small volume
  10. additiontreated with petroleum ether until cloudiness
  11. customA crystalline product formed on storage in the refrigerator overnight
  12. customYield

Sources & evidence

ORD record
ord-9889250ba2dc449bb2d7d2a9635c9889
Source dataset
uspto-grants-1979_04
Patent number
US04148788

Linked notes

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