Triethylamine → BOC-D-alanine

HRID 579851Notes

Reaction equation

HRID 579851 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-52238b58128742b989177e681f0c502f
Source dataset
uspto-grants-1988_06
Patent number
US04749691

Reaction notes

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