Diisopropylethylamine → Boc-Asp(OBzl)-NHMe

HRID 1160399ノート

反応式

HRID 1160399 の反応式
[CH:1]([N:4](CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:34][C:35]([O:38][C:39]([NH:41][C@H:42]([C:54]([OH:56])=O)[CH2:43][C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])=[O:40])([CH3:37])[CH3:36].Cl.CN>CC(N(C)C)=O.C(Cl)Cl>[CH3:34][C:35]([O:38][C:39]([NH:41][C@H:42]([C:54](=[O:56])[NH:4][CH3:1])[CH2:43][C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])=[O:40])([CH3:37])[CH3:36]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 1581888N-tert-Butoxycarbonyl-L-aspartic acid beta-benzyl esterHCID 6364545Methylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 59516205Boc-Asp(OBzl)-NHMe収率 78.3%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 31374Dimethylacetamide溶媒

実験手順

N,N-Diisopropylethylamine (15.10 g, 116.8 mmol) and HATU (10.77 g, 28.34 mmol) were added to a suspension of Boc-Asp-(OBzl)-OH (7.61 g, 23.54 mmol) and methylamine hydrochloride (5.03 g, 74.50 mmol) in DMA (31 mL). After stirring at room temperature for 18 h, the reaction mixture was diluted with CH2Cl2 and washed with saturated NaHCO3. The organic layer was washed with H2O several times, dried over Na2SO4, filtered, and concentrated. The residue was purified via silica gel chromatography with 0% MeOH in CH2Cl2 grading to 4% MeOH in CH2Cl2 to afford the titled product (6.2 g, 78%) as a white solid. 1H-NMR (CDCl3) δ: 1.471 (9H, s), 2.730 (1H, m), 2.818 (3H, d, J=4.8 Hz), 3.120 (1H, m), 4.520 (1H, s), 5.156 (2H, m), 5.660 (1H, s), 6.430 (1H, s), 7.378 (5H, m). LC-MS (ES) m/e 337.2 (M+H)+.

後処理

  1. washwashed with saturated NaHCO3
  2. washThe organic layer was washed with H2O several times
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via silica gel chromatography with 0% MeOH in CH2Cl2 grading to 4% MeOH in CH2Cl2

出典と根拠

ORDレコード
ord-9dfe901d3ae04917b738f55545094cb1
出典データセット
uspto-grants-2010_10
特許番号
US07816395B2

反応ノート

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