Potassium Carbonate → HCID 118036622, compound

HRID 1778039Notes

Reaction equation

HRID 1778039 reaction equation
Br[C:2]([CH3:9])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:10]([O:14][C:15](=[O:20])[NH:16][CH2:17][CH2:18][NH2:19])([CH3:13])([CH3:12])[CH3:11].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:10]([O:14][C:15]([NH:16][CH2:17][CH2:18][NH:19][C:2]([CH3:9])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:20])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 187201N-BOC-ethylenediamine

Product 1

HCID 118036622HCID 118036622, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 2-bromo-2-methylpropanoate (2.0 g, 13.47 mmol) was added to tert-butyl(2-aminoethyl)carbamate (2.0 g, 12.48 mmol) and K2CO3 (4.31 g, 31.2 mmol) in DMF (35 ml) at room temperature. After 18 h at room temperature the reaction mixture was partitioned between aqueous saturated NaHCO3 and EtOAc, extracted 2× with EtOAc, the combined organic layers dried over Na2SO4 and evaporated. The residue was preabsorbed onto isolate and purified by normal phase chromatography: 120 g RediSep® column, eluting with a gradient from DCM to 9:1 DCM containing 0.3% NH3. The product containing fractions were combined and evaporated to give the title compound as a colourless oil. 1H NMR (400 MHz, DMSO-d6) δ 6.74 (t, 1H), 4.07 (q, 2H), 2.95 (q, 2H), 2.45-2.35 (m, 2H), 2.17-2.02 (m, 1H), 1.38 (s, 9H), 1.19 (d, 9H).

Workup

  1. customAfter 18 h at room temperature the reaction mixture was partitioned between aqueous saturated NaHCO3 and EtOAc
  2. extractionextracted 2× with EtOAc
  3. dry with materialthe combined organic layers dried over Na2SO4
  4. customevaporated
  5. customThe residue was preabsorbed
  6. customonto isolate
  7. custompurified by normal phase chromatography
  8. wash120 g RediSep® column, eluting with a gradient from DCM to 9:1 DCM containing 0.3% NH3
  9. additionThe product containing fractions
  10. customevaporated

Sources & evidence

ORD record
ord-f59f4e940a2b4b5ea0a2245440728da0
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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