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4-(Tert-butoxy)-4-oxobutanoic acid → (R)-tert-butyl 4-(1-(4-bromophenyl)-4-ethoxy-4-oxobutan-2-ylamino)-4-oxobutanoate

HRID 881863
ノート
印刷プレビュー

反応式

HRID 881863 の反応式
[C:1]([O:5][C:6](=[O:12])[CH2:7][CH2:8][C:9]([OH:11])=O)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:14][C@H:15]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=1)[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(Cl)Cl>[Br:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][C@@H:15]([NH:14][C:9](=[O:11])[CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:12])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:28][CH:27]=1
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 3

HCID 41391074-(Tert-butoxy)-4-oxobutanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86648197(R)-ethyl 3-amino-4-(4-bromophenyl)butanoate hydrochloride

生成物 1

HCID 59607774(R)-tert-butyl 4-(1-(4-bromophenyl)-4-ethoxy-4-oxobutan-2-ylamino)-4-oxobutanoate収率 72.9%

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4-tert-butoxy-4-oxobutanoic acid (2.38 g, 13.64 mmol) in DMF (30 mL) and DCM (30 mL) is added (R)-ethyl 3-amino-4-(4-bromophenyl)butanoate hydrochloride (4 g, 12.4 mmol), HATU (5.19 g, 13.64 mmol), and TEA (6.91 mL, 49.6 mmol). After stirring at room temperature for 2 hours, the reaction is quenched with H2O, and the crude is diluted with EtOAc, the organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give (R)-tert-butyl 4-(1-(4-bromophenyl)-4-ethoxy-4-oxobutan-2-ylamino)-4-oxobutanoate (4.0 g). HPLC retention time=1.70 minutes (condition A); MS (m+1)=444.1.

後処理

  1. customthe reaction is quenched with H2O
  2. additionthe crude is diluted with EtOAc
  3. washthe organic layer is washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-7302ab906079403898003aad73e4297c
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08993631B2

反応ノート

読み込み中…

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