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

HRID 256490

反応式

HRID 256490 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 10980600BOC-Ala-Gly-OBzl収率 92.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-13ab10030a7b4817b32c19cc963e4370
出典データセット
uspto-grants-1987_10
特許番号
US04703106

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