Tetrahydrofuran → Boc-Leu-Pro-OBn

HRID 435391

Reaction equation

HRID 435391 reaction equation
C1COCC1.[NH:6]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:7]([C:12]([OH:14])=O)[CH2:8][CH:9]([CH3:11])[CH3:10].O.[NH:23]1[CH2:37][CH2:36][CH2:35][C@H:24]1[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>CN(C=O)C>[NH:6]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:7]([C:12]([N:23]1[CH2:37][CH2:36][CH2:35][C@H:24]1[C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])=[O:14])[CH2:8][CH:9]([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 736155Benzyl L-prolinateHCID 12373896N-Boc-L-Leucine Hydrate

Product 1

HCID 10093486Boc-Leu-Pro-OBn

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

THF (300 ml) was added to BOC-Leu-OH.H2O (149.59 g, 0.6 M). THF (150 ml) and DMF (100 ml) were added thereto to prepare a solution. Then H-Pro-OBzl (152.28 g, 0.63 M) was added thereto, and WSCI (120.8 ml, 0.66 M) was added dropwise at -10° C., and further DMF (100 ml) was added; then the mixture was stirred at room temperature overnight. After distilling off the solvent in vacuo, ethyl acetate (600 ml) was added to the residue, which was then washed three times with 5% aqueous sodium bicarbonate, twice with 1 N HCl and twice with water. The ethyl acetate layer was dried with anhydrous sodium sulfate and concentrated in vacuo. The resultant oily material was dissolved in benzene (1 l.) and concentrated in vacuo to obtain an oily substance [1].

Workup

  1. customto prepare a solution
  2. additionWSCI (120.8 ml, 0.66 M) was added dropwise at -10° C.
  3. distillationAfter distilling off the solvent in vacuo, ethyl acetate (600 ml)
  4. additionwas added to the residue, which
  5. washwas then washed three times with 5% aqueous sodium bicarbonate
  6. dry with materialThe ethyl acetate layer was dried with anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. dissolutionThe resultant oily material was dissolved in benzene (1 l.)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3ecd12001bf7452fbeceaa9961288b0f
Source dataset
uspto-grants-1983_08
Patent number
US04400316

Linked notes

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