L-Tartaric acid → HCID 178473026, compound

HRID 2171723Notes

Reaction equation

HRID 2171723 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[CH2:5][O:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[N:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][O:26][C:27](=[O:32])[NH:28][C:29](=[NH:31])[NH2:30])[CH:20]=3)=[CH:15][N:14]=2)[CH2:9][CH2:8]1)[CH3:2].[C:34]([OH:43])(=[O:42])[C@@H:35]([C@H:37]([C:39]([OH:41])=[O:40])[OH:38])[OH:36]>C(O)C>[C:39]([C@@H:37]([C@H:35]([C:34]([OH:43])=[O:42])[OH:36])[OH:38])([OH:41])=[O:40].[C:29]([NH:28][C:27]([O:26][CH2:25][C:21]1[CH:20]=[C:19]([C:16]2[CH:15]=[N:14][C:13]([N:10]3[CH2:9][CH2:8][CH:7]([O:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:33])[CH2:12][CH2:11]3)=[N:18][CH:17]=2)[CH:24]=[CH:23][CH:22]=1)=[O:32])(=[NH:30])[NH2:31]

Participants

4

Reactant 2

HCID 444305L-Tartaric acidHCID 178473025HCID 178473025, compound

Product 1

HCID 178473026HCID 178473026, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl({1-[5-(3-{[(carbamimidoylcarbamoyl)oxy]methyl}phenyl)pyrimidin-2-yl]piperidin-4-yl}oxy)acetate (45 mg) was mixed with ethanol, and L-tartaric acid (15 mg) was added thereto, followed by stirring at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and then diethyl ether was added thereto. The precipitated solid was collected by filtration to obtain ethyl ({1-[5-(3-{[(carbamimidoylcarbamoyl)oxy]methyl}phenyl)pyrimidin-2-yl]piperidin-4-yl}oxy)acetate L-tartrate (28 mg).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiondiethyl ether was added
  4. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-9c6e9cb7990e41db82a866a3d09d8ff7
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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