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Water → Tert-butyl 2-(methoxy(methyl)carbamoyl)morpholine-4-carboxylate

HRID 1527131
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HRID 1527131 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN([C:20]([O:24][N:25]1N=NC2C=CC=N[C:26]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.O>C(Cl)Cl>[CH3:20][O:24][N:25]([CH3:26])[C:14]([CH:10]1[O:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9]1)=[O:16]
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참가 물질

6

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27559654-((Tert-butoxy)carbonyl)morpholine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 57449675Tert-butyl 2-(methoxy(methyl)carbamoyl)morpholine-4-carboxylate수율 84.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-(tert-butoxycarbonyl)morpholine-2-carboxylic acid (10 g, 43 mmol) in DCM (60 mL) was added HATU (19 g, 50 mmol) in portions, The mixture was stirred at room temperature for 0.5 h. Then DIPEA (12.9 g, 100 mmol) and N, O-dimethylhydroxylamine hydrochloride (5.0 g, 51.5 mmol) were added in the mixture. The mixture was stirred at room temperature overnight. Water (40 mL) was added and the mixture was extracted by DCM (100 mL*3). The organic layer was washed with brine (5 mL) and dried over sodium sulfate. Concentration and purification by column chromatography on silica gel (eluted: petroleum ether/ethyl acetate=20/1-10/1) to give tert-butyl 2-(methoxy(methyl)carbamoyl)morpholine-4-carboxylate (10 g, 84%).

후처리

  1. stirringThe mixture was stirred at room temperature overnight
  2. extractionthe mixture was extracted by DCM (100 mL*3)
  3. washThe organic layer was washed with brine (5 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationConcentration and purification by column chromatography on silica gel (eluted: petroleum ether/ethyl acetate=20/1-10/1)

출처 및 근거

ORD 기록
ord-1b348b3be3b3466e8233d08c6a6cd06c
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09085583B2

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