1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → BOC-Ala-Gly-OBzl

HRID 256490

반응식

HRID 256490 반응식
[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:2]([C:4]([OH:6])=O)[CH3:3].CC1C=CC(S(O)(=O)=O)=CC=1.[CH:25]1[CH:30]=[CH:29][C:28]([CH2:31][O:32][C:33]([CH2:35][NH2:36])=[O:34])=[CH:27][CH:26]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C1COCC1>[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:2]([C:4]([NH:36][CH2:35][C:33]([O:32][CH2:31][C:28]1[CH:29]=[CH:30][CH:25]=[CH:26][CH:27]=1)=[O:34])=[O:6])[CH3:3]

참가 물질

6

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 85082Tert-butoxycarbonylalanineHCID 6451311O-benzylglycine toluene-p-sulphonate

생성물 1

HCID 10980600BOC-Ala-Gly-OBzl수율 92.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-5 °C

실험 절차

To a solution of 5.68 g of BOC-Ala-OH, 10.12 g of H-Gly-OBzl.TosOH and 4.0 g of HOBT dissolved in 50 ml of THF, under cooling at -5° C., was added 5.5 ml of WSC, and the mixture was stirred at -5° C. for one hour and at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate. The ethyl acetate layer was washed successively twice with 1N hydrochloric acid, twice with 5% aqueous sodium hydrogen carbonate and with water. After drying over anhydrous magnesium sulfate, the product was concentrated under reduced pressure. The residue was crystallized from n-hexane, then recrystallized twice from ethyl acetate-n-hexane to give 9.32 g (yield: 92.3%) of BOC-Ala-Gly-OBzl melting at 85°-87° C. Rf1 =0.54.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe ethyl acetate layer was washed successively twice with 1N hydrochloric acid, twice with 5% aqueous sodium hydrogen carbonate and with water
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. concentrationthe product was concentrated under reduced pressure
  6. customThe residue was crystallized from n-hexane
  7. customrecrystallized twice from ethyl acetate-n-hexane

출처 및 근거

ORD 기록
ord-13ab10030a7b4817b32c19cc963e4370
출처 데이터셋
uspto-grants-1987_10
특허 번호
US04703106

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