Bromoacetic Acid → HCID 86756571, compound

HRID 322016Notes

Reaction equation

HRID 322016 reaction equation
Br[CH2:2][C:3]([OH:5])=O.[NH:6]([CH2:13][C:14]([O:16]CC)=O)[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].C1CCC(N=C=NC2CCCCC2)CC1.[NH2:34][CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=1>C(Cl)Cl>[O:5]=[C:3]1[CH2:2][N:34]([CH2:35][CH2:36][C:37]2[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=2)[C:14](=[O:16])[CH2:13][N:6]1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

6

Reactant 4

HCID 6227Bromoacetic AcidHCID 10868DicyclohexylcarbodiimideHCID 80502Diethyl iminodiacetateHCID 832754-Pyridineethanamine

Product 1

HCID 86756571HCID 86756571, compoundYield 109.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 25 mL round bottom flask was charged with bromoacetic acid (0.42g, 3.3 mmol), diethyl iminodiacetate (591 μL, 3.0 mmol) and 6 mL of DCM, followed by DCC (0.6809 g, 3.3 mmol). The mixture was stirred at room temperature for about one hour. The white solid DCU was filtered through a glass fritted funnel. The filtrate was concentrated in vacuo and diluted with 4.5 mL dichloromethane, followed by 4-(2-aminoethyl)pyridine (203 μL, 2.0 mmol). The resulting mixture was stirred at room temperature for 18 hour, diluted with DCM and washed with saturated NaHCO3. The aqueous layer was further extracted with DCM and all the organic layers were combined, dried (MgSO4), concentrated in vacuo and chromatographed through 80 g of silica gel eluting with 7% methanol in DCM to afford the title compound as a white solid (0.67 g, 74%).

Workup

  1. filtrationThe white solid DCU was filtered through a glass fritted funnel
  2. concentrationThe filtrate was concentrated in vacuo
  3. additiondiluted with 4.5 mL dichloromethane
  4. stirringThe resulting mixture was stirred at room temperature for 18 hour
  5. washwashed with saturated NaHCO3
  6. extractionThe aqueous layer was further extracted with DCM and all the organic layers
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customchromatographed through 80 g of silica gel eluting with 7% methanol in DCM

Sources & evidence

ORD record
ord-8f4d94fac8d94576955cc4b0db588875
Source dataset
uspto-grants-2001_04
Patent number
US06211183B1

Reaction notes

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