Dicyclohexylcarbodiimide → Boc-Leu-OSu

HRID 851308

Reaction equation

HRID 851308 reaction equation
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].O.O[N:19]1[C:24](=[O:25])[CH2:23][CH2:22][C:20]1=[O:21].C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[NH:1]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[C@H:2]([C:7]([O:9][N:19]1[C:24](=[O:25])[CH2:23][CH2:22][C:20]1=[O:21])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 12373896N-Boc-L-Leucine Hydrate

Product 1

HCID 11023929Boc-Leu-OSuYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Boc-Leu-OH.H2O (49.9 g, 0.2 M) and HOSu (23.0 g, 0.2 M) were dissolved in THF (300 ml) in a 1 lit. round flask. DCC (41.3 g, 0.2 M) in THF (200 ml) solution was added dropwise at -10° C. for about 10 minutes and the mixture was stirred at room temperature overnight. Precipitated DCU was filtered off and the filtrate was concentrated. The residue was dissolved in ethyl acetate (300 ml), washed with 1 N-HCl, NaCl solution and a small amount of water and dried with anhydrous sodium sulfate. After removal of the drying agent, the solution was concentrated, and n-hexane was added thereto to obtain Boc-Leu-OSu as a colorless powder (m.p. 106°-110° C., 59.11 g, yield: 90%).

Workup

  1. filtrationPrecipitated DCU was filtered off
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate (300 ml)
  4. washwashed with 1 N-HCl, NaCl solution
  5. dry with materiala small amount of water and dried with anhydrous sodium sulfate
  6. customAfter removal of the drying agent
  7. concentrationthe solution was concentrated
  8. additionn-hexane was added

Sources & evidence

ORD record
ord-e6ea2c8953da4c4da6b342023bcca484
Source dataset
uspto-grants-1983_05
Patent number
US04384041

Linked notes

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