Citric Acid → HCID 46852365, compound

HRID 241659Notes

Reaction equation

HRID 241659 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][C:3]([CH2:8][C:9]([OH:11])=[O:10])([C:5]([OH:7])=[O:6])[OH:4].[CH3:14][N:15]([CH3:43])[CH2:16][CH2:17][N:18]1[C:22]2[CH:23]=[CH:24][C:25]([S:27]([CH:30]3[CH2:33][N:32]([S:34]([CH3:37])(=[O:36])=[O:35])[CH2:31]3)(=[O:29])=[O:28])=[CH:26][C:21]=2[N:20]=[C:19]1[CH2:38][C:39]([CH3:42])([CH3:41])[CH3:40]>CO>[C:1]([OH:13])(=[O:12])[CH2:2][C:3]([CH2:8][C:9]([OH:11])=[O:10])([C:5]([OH:7])=[O:6])[OH:4].[CH3:14][N:15]([CH3:43])[CH2:16][CH2:17][N:18]1[C:22]2[CH:23]=[CH:24][C:25]([S:27]([CH:30]3[CH2:33][N:32]([S:34]([CH3:37])(=[O:35])=[O:36])[CH2:31]3)(=[O:29])=[O:28])=[CH:26][C:21]=2[N:20]=[C:19]1[CH2:38][C:39]([CH3:41])([CH3:40])[CH3:42]

Participants

4

Reactant 2

HCID 311Citric AcidHCID 46852366HCID 46852366, compound

Product 1

HCID 46852365HCID 46852365, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of citric acid (200 mg, 1.04 mmol) in methanol (3 mL) was added N,N-dimethyl-2-(5-(1-(methylsulfonyl)azetidin-3-ylsulfonyl)-2-neopentyl-1H-benzo[d]imidazol-1-yl)ethanamine (STEP A, 476 mg, 1.04 mmol) and the mixture was concentrated in vacuo. To the residual amorphous was added ethanol (10 mL) and methanol at 60° C. until the solid was dissolved. The solution was cooled to room temperature and the precipitate was filtered. The white solid was dried under reduced pressure to give the title compound (525 mg, 78%).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additionTo the residual amorphous was added ethanol (10 mL) and methanol at 60° C. until the solid
  3. dissolutionwas dissolved
  4. filtrationthe precipitate was filtered
  5. customThe white solid was dried under reduced pressure

Sources & evidence

ORD record
ord-fd5bd0cc31a34591acac8a6c9257fdeb
Source dataset
uspto-grants-2014_02
Patent number
US08653063B2

Reaction notes

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