Dicyclohexylcarbodiimide → BOC-Ala-Gly-OBzl

HRID 867600노트

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HRID 867600 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 10980600BOC-Ala-Gly-OBzl

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8471Triethylamine용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0d6270590ae0427e81ba43fb2895bb4b
출처 데이터셋
uspto-grants-1988_10
특허 번호
US04775743

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