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Dimethylformamide → (2R)-Methyl 3-(tert-butyldimethylsilyloxy)-2-(5-(2-(3,4-dichlorophenyl)propanamido)-1-oxoisoquinolin-2(1H)-yl)propanoate

HRID 1161223
ノート
印刷プレビュー

反応式

HRID 1161223 の反応式
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([C@H:13]([CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[C:14]([O:16][CH3:17])=[O:15])[C:7]2=[O:12].[Cl:27][C:28]1[CH:29]=[C:30]([CH:35]([CH3:39])[C:36](O)=[O:37])[CH:31]=[CH:32][C:33]=1[Cl:34].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.CN(C)C=O>>[Si:20]([O:19][CH2:18][C@@H:13]([N:6]1[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[NH:1][C:36](=[O:37])[CH:35]([C:30]2[CH:31]=[CH:32][C:33]([Cl:34])=[C:28]([Cl:27])[CH:29]=2)[CH3:39])[C:7]1=[O:12])[C:14]([O:16][CH3:17])=[O:15])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]
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 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 217147603,4-Dichloro-alpha-methylbenzeneacetic acidHCID 67087826(R)-Methyl 2-(5-amino-1-oxoisoquinolin-2(1H)-yl)-3-(tert-butyldimethylsilyloxy)propanoate

生成物 1

HCID 67087983
(2R)-Methyl 3-(tert-butyldimethylsilyloxy)-2-(5-(2-(3,4-dichlorophenyl)propanamido)-1-oxoisoquinolin-2(1H)-yl)propanoate

実験手順

A round bottom flask was charged with (R)-methyl 2-(5-amino-1-oxoisoquinolin-2(1H)-yl)-3-(tert-butyldimethylsilyloxy)propanoate (300 mg, 0.0008 mol), 2-(3,4-dichlorophenyl)propanoic acid (200 mg, 0.00092 mol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (600 mg, 0.002 mol), N,N-diisopropylethylamine (0.3 mL, 0.002 mol) and N,N-dimethylformamide (2 mL, 0.03 mol) and the reaction stirred at room temperature over night. The reaction did not go to completion. The solvent was removed and the residue was purified flash chromatography to obtain the product as a solid. MS m/z=578.3 (M+H).

後処理

  1. customThe solvent was removed
  2. customthe residue was purified flash chromatography

出典と根拠

ORDレコード
ord-a90e6ae8f9334c88b6306392df180460
出典データセット
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07816371B2

反応ノート

読み込み中…

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