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Dimethylamine → 1,1-dimethylethyl [5-[(N,N-dimethylglycyl)(methyl)amino]-2-(methyloxy)phenyl]carbamate

HRID 1014390
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HRID 1014390 반응식
[CH3:1][NH:2][C:3]1[CH:4]=[CH:5][C:6]([O:17][CH3:18])=[C:7]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27](Cl)=[O:28].[CH3:30][NH:31][CH3:32].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>O1CCCC1>[CH3:30][N:31]([CH3:32])[CH2:26][C:27]([N:2]([CH3:1])[C:3]1[CH:4]=[CH:5][C:6]([O:17][CH3:18])=[C:7]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:15])[CH3:13])[CH:8]=1)=[O:28]
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참가 물질

7

반응물 5

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 89602Bromoacetyl chlorideHCID 594418351,1-Dimethylethyl [5-(methylamino)-2-(methyloxy)phenyl]carbamateHCID 86584982Sodium bicarbonate ethyl acetate

생성물 1

HCID 594420081,1-dimethylethyl [5-[(N,N-dimethylglycyl)(methyl)amino]-2-(methyloxy)phenyl]carbamate
수율 78%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A suspension of 1,1-dimethylethyl [5-(methylamino)-2-(methyloxy)phenyl]carbamate (2.15 g, 8.52 mmol) and potassium carbonate (2.355 g, 17.04 mmol) in tetrahydrofuran (75 ml) was treated with bromoacetylchioride (0.779 ml, 9.37 mmol), stirred for 45 minutes, and dimethyl amine in THF (17.04 ml, 34.1 mmol) was added. The solution was stirred at room temperature for 8 hours, poured into saturated sodium bicarbonate/ethyl acetate, and the organic layer was separated, dried over sodium sulfate, filtered, taken to a residue under reduced pressure, and purified by column chromatography to afford 1,1-dimethylethyl [5-[(N,N-dimethylglycyl)(methyl)amino]-2-(methyloxy)phenyl]carbamate (2.25 g, 6.67 mmol, 78% yield) as a yellow oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.05 (br. s., 1 H), 7.60 (br. s., 1 H), 6.88-7.10 (m, 2 H), 3.82 (s, 3 H), 3.08 (s, 3 H), 2.80 (br. s., 2 H), 2.11 (s, 6 H), 1.36-1.54 (m, 9 H)

후처리

  1. stirringThe solution was stirred at room temperature for 8 hours
  2. customthe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-8ea5326844d44cda91fc222f99d3ee84
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07981903B2

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