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Triethylamine → HCID 70094445、化合物

HRID 1075638
ノート
印刷プレビュー

反応式

HRID 1075638 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([OH:22])=O)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:25](CC)CC)C.ClC(OCC)=O.N[C@@H:37]1[C:43](=[O:44])[N:42]2[C@@H:38]1[O:39][CH2:40][CH2:41]2>ClCCl.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([C@H:37]1[C:43](=[O:44])[N:42]2[C@@H:38]1[O:39][CH2:40][CH:41]2[NH2:25])=[O:22])[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 21309376HCID 21309376、化合物

生成物 1

HCID 70094445HCID 70094445、化合物収率 17%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
-2.5 °C

実験手順

To a solution of N-benzyloxycarbonyl-L-phenylalanine (867 mg, 2.90 mmole) and triethylamine (323 mg, 3.2 mmole) in dichloromethane (20 ml), ethyl chloroformate (315 mg, 2.90 mmole) was added at -15° C. The reaction mixture was stirred at -10 to 5° C. for 1.5 hrs. Then a precooled (~-15° C.) solution of (5R,6S)-6-amino-4-oxa-1-azabicyclo[3,2,0]heptan-7-one in ethyl acetate (see above) was added at -15° C. and the resulting mixture was stirred at room temperature for 10 hrs. After removal of solvent, the residue was dissolved in ethyl acetate, washed with water, brine and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography using ethyl acetate-hexane (55:45) as eluent and 205 mg of the title compound was obtained as white solid.

後処理

  1. stirringthe resulting mixture was stirred at room temperature for 10 hrs
  2. customAfter removal of solvent
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of solvent
  7. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-d873c7354f284b6aba7483b857444abf
出典データセット
uspto-grants-1999_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05905076

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート