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Trifluoroacetic acid → N-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-D-alanine

HRID 254067
ノート
印刷プレビュー

反応式

HRID 254067 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:11](=[O:12])[C@H:10]([S:13][CH2:14][C:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[O:16])[C@H:9]2[C:24]2[CH:34]=[CH:33][C:27]([O:28]CC(O)=O)=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.[NH2:35][C@@H:36]([C:38]([O:40]C(C)(C)C)=[O:39])[CH3:37].CN1CC[O:49][CH2:48][CH2:47]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:11](=[O:12])[C@H:10]([S:13][CH2:14][C:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[O:16])[C@H:9]2[C:24]2[CH:34]=[CH:33][C:27]([O:28][CH2:47][C:48]([NH:35][C@@H:36]([C:38]([OH:40])=[O:39])[CH3:37])=[O:49])=[CH:26][CH:25]=2)=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 6422Trifluoroacetic acidHCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 7359212tert-butyl (2R)-2-aminopropanoateHCID 66842813[4-((2R,3R)-1-(4-Fluorophenyl)-3-{[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetic acid

生成物 1

HCID 66843258
N-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-D-alanine
収率 99.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetic acid (50 mg, 0.1 mmol), tert-butyl D-alaninate (23 mg, 0.12 mmol) and 4-methylmorpholine (31 mg, 0.31 mmol) were dissolved in DCM (1.5 ml) and stirred at room temperature for 5 minutes. TBTU (40 mg, 0.12 mmol) was added and the reaction mixture was stirred for 2 h. TFA (0.7 ml) was added and the solution was stirred for 90 minutes. TFA and DCM were removed under reduced pressure and the residue was dissolved in DCM and washed with water. The organic layer was dried over sodium sulphate and the solvent was removed under reduced pressure giving 55 mg (95%) of the title product. M/z: 553.0 (M−1).

後処理

  1. stirringthe reaction mixture was stirred for 2 h
  2. stirringthe solution was stirred for 90 minutes
  3. customTFA and DCM were removed under reduced pressure
  4. dissolutionthe residue was dissolved in DCM
  5. washwashed with water
  6. dry with materialThe organic layer was dried over sodium sulphate
  7. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-6a2a9ad763c94ae5a62140d92fa2aa39
出典データセット
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07871998B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート