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

HRID 1614525노트

반응식

HRID 1614525 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 19609075Chloroform toluene methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-400c8067311e4aa5a463c07a88840ec3
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05198208

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