Dimethylamine → Tert-butyl N2-(((9H-fluoren-9-YL)methoxy)carbonyl)-N5,N5-dimethyl-L-glutaminate

HRID 1482234ノート

反応式

HRID 1482234 の反応式
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][C:21](O)=O)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CNC.O.[CH3:62][N:63]([CH3:66])[CH:64]=[O:65]>O1CCCC1>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:20][CH2:21][C:64]([N:63]([CH3:66])[CH3:62])=[O:65])[C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

参加物

7

反応物 5

HCID 674DimethylamineHCID 962WaterHCID 6228DimethylformamideHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 7017910(S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid

生成物 1

HCID 89668280Tert-butyl N2-(((9H-fluoren-9-YL)methoxy)carbonyl)-N5,N5-dimethyl-L-glutaminate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid (Compound SP444) (10.0 g, 23.5 mmol) was dissolved in dimethylformamide (70 ml), ((benzotriazol-1-yloxy)-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) (12.5 g, 28.3 mmol) and dimethylamine (58 mmol) were added as a 2 mol/1 solution in tetrahydrofuran, and the mixture was stirred at room temperature for 30 minutes. Water was added to the reaction solution, followed by extraction with dichloromethane. The organic extract was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to afford tert-butyl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(dimethylamino)-5-oxopentanoate (Compound SP447) (15.2 g) as a crude product.

後処理

  1. extractionfollowed by extraction with dichloromethane
  2. extractionThe organic extract
  3. dry with materialwas dried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-4037fe8148704a29ae1f7fefb9d6590e
出典データセット
uspto-grants-2016_08
特許番号
US09409952B2

反応ノート

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