Dichloromethane → Diisopropylethylamine

HRID 421227

反応式

HRID 421227 の反応式
[C:1]([N:8]1[CH2:13][CH2:12]O[CH2:10][CH:9]1[C:14]([OH:16])=[O:15])([O:3]C(C)(C)C)=O.[CH3:17]N(C(O[N:25]1N=N[C:27]2C=CC=C[C:26]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH:39]([N:42]([CH:45]([CH3:47])[CH3:46])[CH2:43][CH3:44])([CH3:41])[CH3:40].[Cl:48]CCl>>[ClH:48].[CH3:17][O:16][C:14](=[O:15])[C@@H:9]([CH3:10])[NH2:8].[CH:39]([N:42]([CH:45]([CH3:47])[CH3:46])[CH2:43][CH3:44])([CH3:41])[CH3:40].[CH3:27][C@@H:26]1[C:1](=[O:3])[N:8]2[CH2:13][CH2:12][NH:42][CH2:10][CH:9]2[C:14](=[O:16])[NH:25]1

参加物

7

反応物 4

HCID 6344Dichloromethane3 回HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27601334-(tert-Butoxycarbonyl)morpholine-3-carboxylic acid

生成物 3

HCID 81531DiisopropylethylamineHCID 11182647Methyl D-alaninate hydrochlorideHCID 59215897(3R)-3-methyltetrahydro-2H-pyrazino[1,2-a]pyrazine-1,4(3H,6H)-dione

実験手順

To a solution of N-boc-morpholine-3-carboxylic acid (2 g, 9.379 mmol) in 60 mL of dichloromethane and was added TBTU (3.313 g, 10.32 mmol) and diisopropylethyl amine (1.96 mL, 11.25 mmol). The reaction was stirred for 30 min. In the meantime, a solution of D-alanine methyl ester hydrochloride (1.93 g, 18.76 mmol) and diisopropylethylamine (3.27 mL, 18.76 mmol) in 20 mL of dichloromethane was prepared and finally added to the reaction mixture. The reaction was left stirring at room temperature for 2 h. UPLC-MS analysis showed the expected product (peak at 0.60 min, m/z=317 (M+1), 261 (M−t-Bu+1), 217 (M−Boc+1)). The reaction was diluted with dichloromethane and extracted with sat. NaHCO3, dried (Na2SO4), and the solvent removed. The crude (5.56 g) was taken to the next step without further purification.

後処理

  1. additionfinally added to the reaction mixture
  2. waitThe reaction was left
  3. stirringstirring at room temperature for 2 h
  4. extractionextracted with sat. NaHCO3
  5. dry with materialdried (Na2SO4)
  6. customthe solvent removed
  7. customThe crude (5.56 g) was taken to the next step without further purification

出典と根拠

ORDレコード
ord-fca0426383df493bb055573c88de7bea
出典データセット
uspto-grants-2012_01
特許番号
US08097618B2

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