Hydrochloric Acid → HCID 21867201, compound

HRID 857129Notes

Reaction equation

HRID 857129 reaction equation
Cl.[I:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH2:7].C(N(C(C)C)CC)(C)C.Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].Cl>CS(C)=O.O>[I:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH:7][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 27238613-Iodobenzylamine hydrochloride

Product 1

HCID 21867201HCID 21867201, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

3-Iodobenzylamine hydrochloride (1.0 g) and diisopropylethylamine (1.29 ml) were taken up in dry dimethylsulfoxide (60 ml) and treated with ethyl bromoacetate and stirred under nitrogen for 2 h. 2M HCl (1.85 ml) and water (250 ml) were added. This was extracted with EtOAc, the aqueous phase was taken to pH 8 and extracted with EtOAc. The combined extracts were dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by chromatography (Biotage, 40 g) eluting with EtOAc-cyclohexane-diisopropylethylamine (10:89:1 then 20:79:1) to give the title compound (0.571 g) LCMS RT 2.02 min.

Workup

  1. extractionThis was extracted with EtOAc
  2. extractionextracted with EtOAc
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography (Biotage, 40 g)
  6. washeluting with EtOAc-cyclohexane-diisopropylethylamine (10:89:1

Sources & evidence

ORD record
ord-e713a09a906548ae9276e057a58685f4
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

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