4-Methylmorpholine → N,N-dimethyl-beta-alanine, [2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazol-1-yl]-methyl ester

HRID 1493216Notes

Reaction equation

HRID 1493216 reaction equation
[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].CN1CCOCC1.C(OC(Cl)=O)C(C)C.[CH3:24][O:25][C:26]1[C:31]([CH3:32])=[CH:30][N:29]=[C:28]([CH2:33][S:34]([C:36]2[N:40]([CH2:41]O)[C:39]3[CH:43]=[CH:44][CH:45]=[CH:46][C:38]=3[N:37]=2)=[O:35])[C:27]=1[CH3:47].[OH-].[Na+]>C(Cl)Cl>[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][C:5]([O:7][CH2:41][N:40]1[C:39]2[CH:43]=[CH:44][CH:45]=[CH:46][C:38]=2[N:37]=[C:36]1[S:34]([CH2:33][C:28]1[C:27]([CH3:47])=[C:26]([O:25][CH3:24])[C:31]([CH3:32])=[CH:30][N:29]=1)=[O:35])=[O:6]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 14798Sodium HydroxideHCID 62365Isobutyl chloroformateHCID 2398283-(Dimethylamino)propanoic acidHCID 15282209HCID 15282209, compound

Product 1

HCID 56993588N,N-dimethyl-beta-alanine, [2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazol-1-yl]-methyl esterYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-10 °C

Procedure

N,N-dimethyl-β-alanine (0.76 g 0.005 mol) and N-methyl morpholine (0.99 g 0.01 mol) was added to CH2Cl2 (15 ml). The solution was cooled to -10° C. and isobutylchloroformate, (0.68 g 0.005 mol) dissolved in CH2Cl2 (15 ml), was added under inert atmosphere. The solution was stirred for about 20 min at -10° C. [2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]-sulfinyl]-1H-benzimidazol-1-yl]methanol dissolved in CH2Cl2 (15 ml) was added dropwise to the mixed anhydride at -10° C. The solution was stirred 2 h at -10°, and the temperature was thereafter raised to room temperature. NaOH solution (25 ml 0.24) was added under stirring and the mixture was stirred for about 5 min. After separation the CH2Cl2 phase was dried over Na2SO4, filtered and the solution was evaporated off, giving the desired compound (yield 0.7 g 32%). The identity of the title compound was confirmed with NMR.

Workup

  1. additionwas added under inert atmosphere
  2. temperaturethe temperature was thereafter raised to room temperature
  3. stirringunder stirring
  4. stirringthe mixture was stirred for about 5 min
  5. customAfter separation the CH2Cl2 phase
  6. dry with materialwas dried over Na2SO4
  7. filtrationfiltered
  8. customthe solution was evaporated off

Sources & evidence

ORD record
ord-387b34c927814828aae85fd828baf022
Source dataset
uspto-grants-1991_06
Patent number
US05021433

Reaction notes

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