4-Methylmorpholine → N,N'-Dicyclohexylurea

HRID 617112

反応式

HRID 617112 の反応式
[CH2-]C(C)=[O:3].CN1CCOCC1.ON1C2C=CC=CC=2N=N1.[CH2:22]1[CH2:27][CH2:26][CH:25]([N:28]=[C:29]=[N:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[CH2:24][CH2:23]1>CC(C)=O.C1COCC1>[C:29]([NH:28][CH:25]1[CH2:24][CH2:23][CH2:22][CH2:27][CH2:26]1)([NH:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)=[O:3]

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 178477758HCID 178477758、化合物

生成物 1

HCID 4277N,N'-Dicyclohexylurea

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of freshly prepared acetonide-protected amino acid (0.2 mmol, 1 equiv) in acetone (1.5 mL) was added 3 mL of THF, N-methylmorpholine (0.22 mmol, 1.1 equiv), 1-hydroxybenzotriazole (0.44 mmol, 2.2 equiv), and hexapeptide amine (0.22 mmol, 1.1 equiv). The resultant mixture was cooled to 0° C. and DCC (0.22 mmol, 1.1 equiv) was added. The mixture was allowed to warm up to room temperature and stirred under N2 for 20 h, after which time the precipitated dicyclohexylurea (DCU) was removed by filtration and washed with small portion of CH2Cl2. The combined filtrate was washed with saturated NaHCO3 solution and dried over MgSO4. Concentration in vacuo and dissolution of the residue in EtOAc yielded more DCU. The residue remaining after a second filtration and concentration in vacuo was purified by chromatography with 10-40% acetone in freshly distilled n-hexane to give the N,O-Isopropylidene-protected heptapeptide 1-7 (SEQ ID NO:10).

後処理

  1. customafter which time the precipitated dicyclohexylurea (DCU) was removed by filtration
  2. washwashed with small portion of CH2Cl2
  3. washThe combined filtrate was washed with saturated NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. concentrationConcentration
  6. dissolutionin vacuo and dissolution of the residue in EtOAc

出典と根拠

ORDレコード
ord-b99bcbe6cc764619a6512372c8babae6
出典データセット
uspto-grants-1999_09
特許番号
US05948693

関連ノート

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