Oxalic Acid → Methyl 2-benzyloxy-5-[2-[1,1-dimethyl-3-[1,2,4]triazol-1-yl-propylamino]-1-hydroxy-ethyl]-benzoate

HRID 1787845Notes

Reaction equation

HRID 1787845 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]([C:19](=[O:25])[CH:20](OCC)O)=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][C:27]([NH2:36])([CH3:35])[CH2:28][CH2:29][N:30]1[CH:34]=[N:33][CH:32]=[N:31]1.C(O)(=O)C(O)=O>C(O)C>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]([CH:19]([OH:25])[CH2:20][NH:36][C:27]([CH3:35])([CH3:26])[CH2:28][CH2:29][N:30]2[CH:34]=[N:33][CH:32]=[N:31]2)=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 597541992-methyl-4-(1H-1,2,4-triazol-1-yl)butan-2-amineHCID 68858509Methyl benzyloxy-5-(2-ethoxy-2-hydroxy-acetyl)-benzoate

Product 1

HCID 68877359Methyl 2-benzyloxy-5-[2-[1,1-dimethyl-3-[1,2,4]triazol-1-yl-propylamino]-1-hydroxy-ethyl]-benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

9.5 g of methyl 2-benzyloxy-5-(2-ethoxy-2-hydroxy-acetyl)-benzoate and 3.1 g of 1,1-dimethyl-3-[1,2,4]triazol-1-yl-propylamine are reacted and worked up analogously to the method described for Example 2a. The crude product is dissolved in 100 mL 95% ethanol and combined with an ethanolic solution of 1.8 g of oxalic acid. After the addition of a crystallisation aid the precipitated product is separated off and washed. Yield: 8 g (64%, bisoxalate), m.p.=220-222° C.

Workup

  1. additionAfter the addition of a crystallisation aid the precipitated product
  2. customis separated off
  3. washwashed

Sources & evidence

ORD record
ord-e9eb6ee0f02c4baba66eefb6b40f809a
Source dataset
uspto-grants-2009_03
Patent number
US07511067B2

Reaction notes

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