Diisopropylethylamine → Boc-Asp(OBzl)-NHMe

HRID 1160399노트

반응식

HRID 1160399 반응식
[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]

참가 물질

7

반응물 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)

생성물 1

HCID 59516205Boc-Asp(OBzl)-NHMe수율 78.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 31374Dimethylacetamide용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-9dfe901d3ae04917b738f55545094cb1
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816395B2

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