Leucine, N-carboxy-, N-benzyl ester, L- → HCID 131715719, compound

HRID 622638Notes

Reaction equation

HRID 622638 reaction equation
[NH:1]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C@H:2]([C:7]([OH:9])=O)[CH2:3][CH:4]([CH3:6])[CH3:5].[NH2:20][C@H:21]([C:26]([N:28]1[CH2:36][CH2:35][CH2:34][C@H:29]1[C:30]([O:32][CH3:33])=[O:31])=[O:27])[CH2:22][CH:23]([CH3:25])[CH3:24].N(C(OCC1C=CC=CC=1)=O)[C@H](C(O)=O)C(C)C>C(Cl)Cl>[NH:1]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C@H:2]([C:7]([NH:20][C@H:21]([C:26]([N:28]1[CH2:36][CH2:35][CH2:34][C@H:29]1[C:30]([O:32][CH3:33])=[O:31])=[O:27])[CH2:22][CH:23]([CH3:24])[CH3:25])=[O:9])[CH2:3][CH:4]([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 74840Leucine, N-carboxy-, N-benzyl ester, L-HCID 726987N-Carbobenzoxy-L-valineHCID 14302360HCID 14302360, compound

Product 1

HCID 131715719HCID 131715719, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Z-Leu-OH (1 equivalent), H-Leu-Pro-OMe (1 equivalent) synthesized in (a) and TEA (1 equivalent) were dissolved in dry methylene chloride, and WSCD (1 equivalent) was added under cooling with ice. Thereafter, the mixture was stirred at room temperature for 20 hours, and the reaction mixture was washed successively with IN HCl, water, saturated aqueous sodium bicarbonate, water and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off under vacuum. The resulting crude product was purified by medium-pressure liquid column chromatography to obtain the end compound. Z-Leu-Leu-Pro-OMe (1 equivalent) thus obtained was dissolved in ethanol, and boron trifluoride-ether complex (1 equivalent) and palladium on carbon (a small amount) were added. The mixture was subjected to catalytic reduction in a hydrogen atmosphere to remove the Z group, and the solvent was distilled off under vacuum to obtain the end compound as an oil.

Workup

  1. additionWSCD (1 equivalent) was added
  2. temperatureunder cooling with ice
  3. washthe reaction mixture was washed successively with IN HCl, water, saturated aqueous sodium bicarbonate, water and saturated brine
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under vacuum
  6. customThe resulting crude product was purified by medium-pressure liquid column chromatography
  7. customto obtain the end compound

Sources & evidence

ORD record
ord-5bfbe36529b1429faaf2c9b82f2111ba
Source dataset
uspto-grants-1988_09
Patent number
US04772587

Reaction notes

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