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

HRID 1014390Notes

Reaction equation

HRID 1014390 reaction equation
[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]

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-8ea5326844d44cda91fc222f99d3ee84
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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