Chloroacetic Acid → HCID 66567442, compound

HRID 1771863Notes

Reaction equation

HRID 1771863 reaction equation
[Cl:1][CH2:2][C:3]([OH:5])=O.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[C:28]([NH:31][CH:32]1[CH2:36][CH2:35][NH:34][CH2:33]1)(=[O:30])[CH3:29]>C(Cl)Cl.C1COCC1>[Cl:1][CH2:2][C:3]([N:34]1[CH2:35][CH2:36][CH:32]([NH:31][C:28](=[O:30])[CH3:29])[CH2:33]1)=[O:5]

Participants

7

Reactant 4

HCID 300Chloroacetic AcidHCID 757711-HydroxybenzotriazoleHCID 5227153-AcetamidopyrrolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 66567442HCID 66567442, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of chloroacetic acid (0.715 g, 7.56 mmol, 1 eq.) in DCM (15 mL) and THF (12 mL) at r.t. was added EDC.HCl (1.89 g, 9.83 mmol, 1.3 eq.) and HOBt (1.33 g, 9.83 mmol, 1.3 eq.). The reaction mixture was stirred at r.t. for 30 min and then 3-acetamidopyrrolidine (1.26 g, 9.83 mmol, 1.3 eq.) was added. After stirring two days at r.t., the reaction mixture was diluted with water, HCl 1 M, and DCM. The aqueous phase was extracted with DCM five times. The combined organic layers were washed with a saturated NaHCO3 solution, with brine, dried over Na2SO4, filtered and concentrated in vacuo. The resulting crude oil was used as such in the next step.

Workup

  1. stirringAfter stirring two days at r.t.
  2. extractionThe aqueous phase was extracted with DCM five times
  3. washThe combined organic layers were washed with a saturated NaHCO3 solution, with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d6c7246baf5f4a10846975ceaacd1af3
Source dataset
uspto-grants-2016_02
Patent number
US09249141B2

Reaction notes

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