4-(Benzyloxy)butanoic acid → HCID 11142747, compound

HRID 1912047Notes

Reaction equation

HRID 1912047 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([C@H:22]1[CH2:26][O:25][C:24](=[O:27])[NH:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CCN=C=NCCCN(C)C.Cl>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[CH2:15]([C@H:22]1[CH2:26][O:25][C:24](=[O:27])[N:23]1[C:12](=[O:14])[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:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 5622014-(Benzyloxy)butanoic acidHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 11142747HCID 11142747, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

4-Benzyloxybutyric acid (238 g), (S)-4-benzyl-2-oxazolidinone (217 g) and chloroform (1300 mL) were mixed. After an addition of 4-dimethylaminopyridine (45 g) and WSC.HCl (282 g) to the mixture at ice temperature, the resulting mixture was stirred at RT overnight. The reaction mixture was concentrated in vacuo and toluene (2 L) was poured into the residue. The mixture was washed with 1 N hydrochloric acid (1.5 L), saturated aqueous sodium bicarbonate (2 L) and brine (1.5 L), then dried over sodium sulfate. The sodium sulfate was filtered off and the filtrate was concentrated in vacuo to give the title compound (424.8 g) as a crude product.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo and toluene (2 L)
  2. additionwas poured into the residue
  3. washThe mixture was washed with 1 N hydrochloric acid (1.5 L), saturated aqueous sodium bicarbonate (2 L) and brine (1.5 L)
  4. dry with materialdried over sodium sulfate
  5. filtrationThe sodium sulfate was filtered off
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-de5617940ad94ae182762b8552cdf1db
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

Loading…