Triethylamine → BOC-D-alanine

HRID 979250Notes

Reaction equation

HRID 979250 reaction equation
C(N(CC)CC)C.[CH3:8][C@@H:9]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:10]([O:12]N1C(=O)CCC1=O)=[O:11]>O1CCOCC1>[CH3:8][C@@H:9]([NH:20][C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 11580086N-[(1,1-Dimethylethoxy)carbonyl]-D-alanine 2,5-dioxo-1-pyrrolidinyl ester

Product 1

HCID 637606BOC-D-alanine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of Z--(L)--mesoDAP (2) (1.50 g) and triethylamine (1.0 g) in aqueous dioxane (dioxane 30 ml and water 20 ml) was added Boc--D--Ala--OSu (3) (1.32 g) and the mixture was allowed to stand overnight at room temperature. Dioxane was evaporated, and the resulting aqueous solution was acidified with diluted hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and evaporated to give Boc--D--Ala--(D)--Z--(L)--mesoDAP (4) (1.90 g) as a white foam.

Workup

  1. additionTo a mixture of Z
  2. customDioxane was evaporated
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-037a890e538b4932bf3075ad8ae16c3f
Source dataset
uspto-grants-1987_05
Patent number
US04666890

Reaction notes

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