Dicyclohexylcarbodiimide → BOC-Ala-Gly-OBzl

HRID 867600Notes

Reaction equation

HRID 867600 reaction equation
S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH2:12]([O:19][C:20](=[O:23])[CH2:21][NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:24]([O:28][C:29]([NH:31][C@H:32]([C:34](O)=[O:35])[CH3:33])=[O:30])([CH3:27])([CH3:26])[CH3:25].ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C.C(N(CC)CC)C>[CH2:12]([O:19][C:20](=[O:23])[CH2:21][NH:22][C:34](=[O:35])[C@H:32]([CH3:33])[NH:31][C:29]([O:28][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:30])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 85082Tert-butoxycarbonylalanineHCID 6451311O-benzylglycine toluene-p-sulphonate

Product 1

HCID 10980600BOC-Ala-Gly-OBzl

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 12.9 g of glycine benzyl ester tosylate in 200 ml acetonitrile cooled to 0° C., was added dropwise triethylamine (5.3 ml), followed by addition of 12 g of N-tert-butyloxycarbonylalanine N-hydroxysuccinimide ester (prepared by reaction of N-tert-butyloxycarbonylalanine with N-hydroxysuccinimide in the presence of dicyclohexylcarbodiimide). The resulting solution was stirred at 0° C. for one hour and then at room temperature for 18 hours. At the end of reaction, the solvent was distilled off under reduced pressure, the residue was extracted with ethyl acetate, and the extract was washed with 5% acetic acid, water and saturated aqueous solution of sodium chloride in that order, giving 16 g of crude product. Purification of this crude product by silica gel chromatography (chloroform:methanol=40:1) afforded 12.6 g of pure N-tert-butyloxycarbonyl-L-alanyl-glycine benzyl ester.

Workup

  1. waitat room temperature for 18 hours
  2. customAt the end of reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washthe extract was washed with 5% acetic acid, water and saturated aqueous solution of sodium chloride in that order
  6. customgiving 16 g of crude product
  7. customPurification of this crude product by silica gel chromatography (chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-0d6270590ae0427e81ba43fb2895bb4b
Source dataset
uspto-grants-1988_10
Patent number
US04775743

Reaction notes

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