O-benzyl-L-serine → N-(tert-Butoxycarbonyl)-L-leucyl-O-benzyl-L-serine

HRID 2083814Notes

Reaction equation

HRID 2083814 reaction equation
[NH2:1][C@H:2]([C:12]([OH:14])=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)(O)[O-].[Na+].[CH3:20][CH:21]([CH2:23][C@H:24]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:25](ON1C(=O)CCC1=O)=[O:26])[CH3:22]>O.O1CCOCC1.CN(C=O)C>[NH:35]([C:36]([O:38][C:39]([CH3:41])([CH3:40])[CH3:42])=[O:37])[C@H:24]([C:25]([NH:1][C@H:2]([C:12]([OH:14])=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:26])[CH2:23][CH:21]([CH3:22])[CH3:20]

Participants

7

Reactant 3

HCID 78457O-benzyl-L-serineHCID 516892Sodium BicarbonateHCID 11023929Boc-Leu-OSu

Product 1

HCID 15003967N-(tert-Butoxycarbonyl)-L-leucyl-O-benzyl-L-serineYield 78.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent2×

Procedure

H-Ser(Bzl)-OH (11.7 g.) was dissolved in water (50 ml.) and sodium bicarbonate (10.1 g.) and dioxane (10 ml.) added thereto. BOC-Leu-OSU (16.4 g.) in dioxane (15 ml.) and DMF (5 ml.) were then added. After overnight stirring, the pH of the reaction mixture was adjusted to pH 7, and the mixture concentrated in vacuo to remove organic solvent. The aqueous layer was shaken with ethyl acetate (100 ml.) and the organic layer was washed twice with 1 N HCl and water. The organic layer was dried with anhydrous magnesium sulfate, concentrated in vacuo and the residue was twice recrystallized from ethyl acetate - n-hexane to obtain BOC-Leu-Ser(Bzl)-OH (16.1 g., Yield: 78.8%, m.p.: 82° - 86° C.).

Workup

  1. concentrationthe mixture concentrated in vacuo
  2. customto remove organic solvent
  3. stirringThe aqueous layer was shaken with ethyl acetate (100 ml.)
  4. washthe organic layer was washed twice with 1 N HCl and water
  5. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customthe residue was twice recrystallized from ethyl acetate - n-hexane

Sources & evidence

ORD record
ord-497d916d403343e693e1ce0fe08e9f19
Source dataset
uspto-grants-1978_04
Patent number
US04086221

Reaction notes

Loading…