1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 71114729, compound

HRID 1912071Notes

Reaction equation

HRID 1912071 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([C@@H:23]1[CH2:27][O:26][C:25](=[O:28])[NH:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN=C=NCCCN(C)C.Cl>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[CH2:16]([C@@H:23]1[CH2:27][O:26][C:25](=[O:28])[N:24]1[C:13](=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734969(R)-4-Benzyl-2-oxazolidinoneHCID 104205755-(Benzyloxy)pentanoic acid

Product 1

HCID 71114729HCID 71114729, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

5-Benzyloxyvaleric acid (87.97 g), (R)-4-benzyl-2-oxazolidinone (74.8 g) and chloroform (880 mL) were mixed. To the mixture were added 4-dimethylaminopyridine (51.5 g) and WSC.HCl (85 g). The mixture was stirred at RT for 2.5 hr. The reaction mixture was concentrated in vacuo. To the resultant residue was added ethyl acetate (360 mL). To the mixture were added 2 N hydrochloric acid (211 mL) and water (100 mL), and the mixture was extracted with ethyl acetate (180 mL). The organic layer was washed with 2 N hydrochloric acid (105 mL), water (90 mL), saturated aqueous sodium bicarbonate (90 mL×2) and brine (90 mL), then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo to give the title compound (148 g) as a crude product.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionTo the resultant residue was added ethyl acetate (360 mL)
  3. additionTo the mixture were added 2 N hydrochloric acid (211 mL) and water (100 mL)
  4. extractionthe mixture was extracted with ethyl acetate (180 mL)
  5. washThe organic layer was washed with 2 N hydrochloric acid (105 mL), water (90 mL), saturated aqueous sodium bicarbonate (90 mL×2) and brine (90 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationThe magnesium sulfate was filtered off
  8. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0ba52421b0304a2989b914dd6fe15593
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

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