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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (S)-tert-Butyl 4-oxo-9-(trifluoromethyl)-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamate

HRID 1055421
ノート
印刷プレビュー

反応式

HRID 1055421 の反応式
[NH2:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[C:3]=1[O:4][CH2:5][C@H:6]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:7](O)=[O:8].CCN=C=NCCCN(C)C>CN(C=O)C.CCOC(C)=O>[O:8]=[C:7]1[C@@H:6]([NH:10][C:11](=[O:12])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:5][O:4][C:3]2[C:18]([C:22]([F:25])([F:24])[F:23])=[CH:19][CH:20]=[CH:21][C:2]=2[NH:1]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 21091528(S)-3-(2-amino-6-(trifluoromethyl)phenoxy)-2-(tert-butoxycarbonylamino)propanoic acid

生成物 1

HCID 67077046(S)-tert-Butyl 4-oxo-9-(trifluoromethyl)-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamate収率 89%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒
HCID 8857
Ethyl Acetate
溶媒

実験手順

A solution of (S)-3-(2-amino-6-(trifluoromethyl)phenoxy)-2-(tert-butoxycarbonylamino)propanoic acid (1.23 g, 3.38 mmol) and EDCI (803 mg, 4.19 mmol) in DMF (25 mL) was stirred at RT for 6 h, diluted with EtOAc and washed with H2O. The combined aqueous washes were extracted with EtOAc and the combined organic solutions were dried over MgSO4, filtered. The filtrate was concentrated to give a residue that was purified by silica gel chromatography to afford the title compound (1.04 g, 89%) as a light brown oil. MS m/z 369 (M+Na)+

後処理

  1. washwashed with H2O
  2. extractionThe combined aqueous washes were extracted with EtOAc
  3. dry with materialthe combined organic solutions were dried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customto give a residue that
  7. customwas purified by silica gel chromatography

出典と根拠

ORDレコード
ord-bcff59f9e1d34f8b8f58a662159fbaae
出典データセット
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09394263B2

反応ノート

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