Trimethyl orthoformate → HCID 84421469, compound

HRID 525993Notes

Reaction equation

HRID 525993 reaction equation
[O:1]=[C:2]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][N:10]=1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH:19](OC)(OC)OC.S(Cl)(Cl)=O>CO>[O:1]=[C:2]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:11][N:10]=1)[CH2:3][CH2:4][C:5]([O:7][CH3:19])=[O:6]

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 24386Thionyl ChlorideHCID 84352846HCID 84352846, compound

Product 1

HCID 84421469HCID 84421469, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Oxo-4-[[5-(trifluoromethyl)-2-pyridyl]amino]butanoic acid (Example 11, A19, 50 mg, 0.19 mmol) and trimethyl orthoformate (60.7 mg, 3 eq.) were dissolved in methanol (4 mL), and thionyl chloride (68.1 mg, 3 eq.) was added dropwise. The reaction was stirred at room temperature for 3 h. The solvent were evaporated and the crude was treated with Dowex 1×8 OH to give the methyl 4-oxo-4-[[5-(trifluoromethyl)-2-pyridyl]amino]butanoate A20 (36 mg, 69%). 1H NMR (400 MHz, CDCl3): 2.77 (s, 4H), 3.73 (s, 3H), 7.91 (dd, 1H), 8.33 (d, 1H), 8.54 (s, 1H), 8.59 (s, 1H).

Workup

  1. customThe solvent were evaporated
  2. additionthe crude was treated with Dowex 1×8 OH

Sources & evidence

ORD record
ord-030a39c92be8478a94b8932a6b502b82
Source dataset
uspto-grants-2016_05
Patent number
US09345244B2

Reaction notes

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