Trityl chloride → 2-(2-Hydroxyethyl)3-oxo-1,7-bis(triphenylmethyl)-1,4,7-triazaheptane

HRID 1614525ノート

反応式

HRID 1614525 の反応式
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:30])[CH:6]([CH2:27][CH2:28][OH:29])[NH:7][C:8]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:31]1([C:37](Cl)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CN1CCOCC1>CN(C=O)C.C(Cl)(Cl)Cl.C1(C)C=CC=CC=1.CO>[OH:29][CH2:28][CH2:27][CH:6]([C:5](=[O:30])[NH:4][CH2:3][CH2:2][NH:1][C:37]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[NH:7][C:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

6

反応物 3

HCID 6456Trityl chlorideHCID 79724-MethylmorpholineHCID 194385476-Amino-2-(2-hydroxyethyl)-3-oxo-1-(triphenylmethyl)-1,4-diazahexane

生成物 1

HCID 194385132-(2-Hydroxyethyl)3-oxo-1,7-bis(triphenylmethyl)-1,4,7-triazaheptane収率 27.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 19609075Chloroform toluene methanol溶媒

実験手順

6-Amino-2-(2-hydroxyethyl)-3-oxo-1-(triphenylmethyl)-1,4-diazahexane (15.0 g, 37.2 mmol) (Example 9 (a)) was dissolved in 150 ml DMF and triphenylmethyl chloride (10.35 g, 37.2 mmol) and methylmorpholine (3.75 g, 37.2 mmol) was added. After being stirred for 24 hours at ambient temperature, the reaction mixture was filtered and poured into 200 ml of ice water. After 1 hour stirring, filtration and thoroughly washing the precipitate with water, the solid was dried in vacuo at 50° C. to yield 22 g of crude product. The product was dissolved in chloroform/toluene/methanol (80/16/14) and purified on silica to yield 6.6 g (27%) of 2-(2-hydroxyethyl)3-oxo-1,7-bis(triphenylmethyl)-1,4,7-triazaheptane as white crystals, m.p. 71°-72° C., FAB MS: 646(M+1). The structure was confirmed by 13C NMR.

後処理

  1. filtrationthe reaction mixture was filtered
  2. additionpoured into 200 ml of ice water
  3. stirringAfter 1 hour stirring
  4. filtrationfiltration
  5. washthoroughly washing the precipitate with water
  6. customthe solid was dried in vacuo at 50° C.
  7. customto yield 22 g of crude product
  8. custompurified on silica

出典と根拠

ORDレコード
ord-400c8067311e4aa5a463c07a88840ec3
出典データセット
uspto-grants-1993_03
特許番号
US05198208

反応ノート

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