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Diisopropylethylamine → (S)-tert-butyl 2-allyl-3-(2-(3-(3-bromo-5-fluorophenyl)-1-methoxy-1-oxopropan-2-ylamino)-2-oxoethyl)-1H-indole-1-carboxylate

HRID 1471648
ノート
印刷プレビュー

反応式

HRID 1471648 の反応式
[CH2:1]([C:4]1[N:5]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:6]2[C:11]([C:12]=1[CH2:13][C:14](O)=[O:15])=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:2]=[CH2:3].Cl.[NH2:25][C@@H:26]([CH2:31][C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[C:34]([Br:39])[CH:33]=1)[C:27]([O:29][CH3:30])=[O:28].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:1]([C:4]1[N:5]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:6]2[C:11]([C:12]=1[CH2:13][C:14]([NH:25][C@@H:26]([CH2:31][C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[C:34]([Br:39])[CH:33]=1)[C:27]([O:29][CH3:30])=[O:28])=[O:15])=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:2]=[CH2:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90280217(S)-methyl 2-amino-3-(3-bromo-5-fluorophenyl)propanoate hydrochlorideHCID 902812522-(2-allyl-1-(tert-butoxycarbonyl)-1H-indol-3-yl)acetic acid

生成物 1

HCID 90281512
(S)-tert-butyl 2-allyl-3-(2-(3-(3-bromo-5-fluorophenyl)-1-methoxy-1-oxopropan-2-ylamino)-2-oxoethyl)-1H-indole-1-carboxylate
収率 65.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-(2-allyl-1-(tert-butoxycarbonyl)-1H-indol-3-yl)acetic acid (850 mg, 2.7 mmol) and (S)-methyl 2-amino-3-(3-bromo-5-fluorophenyl)propanoate hydrochloride (720 mg, 2.61 mmol) were combined in DCM (13 mL) and treated with HATU (1.49 g, 3.9 mmol) and iPr2NEt (1.13 mL, 6.5 mmol). After stirring for 16 h at room temperature, the reaction was partitioned between DCM and H2O. The organics were separated and dried over sodium sulfate. After removal of solvent, the crude product was purified by silica gel chromatography to provide (S)-tert-butyl 2-allyl-3-(2-(3-(3-bromo-5-fluorophenyl)-1-methoxy-1-oxopropan-2-ylamino)-2-oxoethyl)-1H-indole-1-carboxylate (0.98 g, 63%). MS (m/z) 573 [M+H]+.

後処理

  1. customthe reaction was partitioned between DCM and H2O
  2. customThe organics were separated
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of solvent
  5. customthe crude product was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-22085af253ca44158aa15914e9964284
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09012441B2

反応ノート

読み込み中…

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