Sodium Iodide → N-2-Propen-1-ylglycine ethyl ester

HRID 1896218Notes

Reaction equation

HRID 1896218 reaction equation
C([O-])([O-])=O.[K+].[K+].[Na+].[I-].C(N(CC)CC)C.[CH2:16]([NH2:19])[CH:17]=[CH2:18].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C=O)C>[CH2:16]([NH:19][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:17]=[CH2:18]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 7748Ethyl bromoacetateHCID 7853AllylamineHCID 8471TriethylamineHCID 11430Potassium Carbonate

Product 1

HCID 10975597N-2-Propen-1-ylglycine ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To an ice cold solution of K2CO3 (331.7 g, 2.4 mol), NaI (360 g, 2.4 mol), DMF (1 L), triethylamine (484.8 g, 4.8 mol) and prop-2-en-1-amine (82 g, 1.44 mol) was slowly added a solution of ethyl bromoacetate (200 g, 1.2 mol) in DMF (100 mL) via addition funnel over 0.5 hr. The ice bath was removed upon completion of addition, and the mixture was stirred at room temperature overnight. The mixture was filtered and rinsed with Et2O. Cold saturated NaCl aq. (2 L) was added to filtrate and the mixture was extracted with Et2O (1 L*3). The combined organic extracts were dried over Na2SO4, filtered and concentrated which gave the title compound XId (150 g, 87.3%) as a yellow oil, which was directly utilized for next reaction without further purification.

Workup

  1. additionvia addition funnel over 0.5 hr
  2. customThe ice bath was removed upon completion of addition
  3. filtrationThe mixture was filtered
  4. washrinsed with Et2O
  5. additionCold saturated NaCl aq. (2 L) was added to filtrate
  6. extractionthe mixture was extracted with Et2O (1 L*3)
  7. dry with materialThe combined organic extracts were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated which

Sources & evidence

ORD record
ord-af0ea92cf32b48a1a64bd532a2623c9d
Source dataset
uspto-grants-2013_08
Patent number
US08518952B2

Reaction notes

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