Trifluoroacetic acid → 6,12-Bis(benzyloxy)-7-oxo-6,12-diazadodecanenitrile

HRID 2380137ノート

反応式

HRID 2380137 の反応式
FC(F)(F)C(O)=O.C(OC([N:15]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:36])[N:21]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27])=O)(C)(C)C>C(Cl)Cl>[CH2:29]([O:28][N:21]([C:20](=[O:36])[CH2:19][CH2:18][CH2:17][CH2:16][NH:15][O:37][CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[CH2:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 1032403412-(tert-Butoxycarbonyl)-6,12-bis(benzyloxy)-7-oxo-6,12-diazadodecanenitrile

生成物 1

HCID 103414656,12-Bis(benzyloxy)-7-oxo-6,12-diazadodecanenitrile

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Trifluoroacetic acid (25 mL) was slowly dripped into a solution of (4) (7.10 g, 13.93 mmol) in CH2Cl2 (150 mL) which had been cooled to 0° C. The solution was stirred at 0° C. for 30 minutes and at room temperature for 15 minutes. Solvent and excess TFA were removed by rotary evaporation, and the concentrate was cooled to 0° C., treated with saturated NaHCO3 (150 mL) and extracted with CH2Cl2 (4×80 mL). After solvent removal, the crude oil was purified by silica gel column chromatography with 1:1 hexane/EtOAc as the eluant, generating 4.6 g (81%) of (5) as an oil: NMR δ 1.40-190 (m, 8H), 2.30 (t, 2H, J=6), 2.40 (t, 2H, J=6), 2.90 (t, 2H, J=6), 3.63 (t, 2H, J= 6), 4.63 (s, 2H), 4.75 (s, 2H), 4.93 (br s, 1H), 7.27 (s, 5H), 7.33 (s, 5H). Anal. (C24H31N3O3) C, H, N.

後処理

  1. customSolvent and excess TFA were removed by rotary evaporation
  2. temperaturethe concentrate was cooled to 0° C.
  3. additiontreated with saturated NaHCO3 (150 mL)
  4. extractionextracted with CH2Cl2 (4×80 mL)
  5. customAfter solvent removal
  6. customthe crude oil was purified by silica gel column chromatography with 1:1 hexane/EtOAc as the eluant

出典と根拠

ORDレコード
ord-5c8718210fd24bf8ae0596005dee5abd
出典データセット
uspto-grants-1994_11
特許番号
US05364965

反応ノート

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