2-(5-Cyanopentyl)-2-(3-methyl[1,2,4]thiadiazol-5-yl)malonic acid di-tert-butyl ester → 7-Cyano-2-(3-methyl[1,2,4]thiadiazol-5-yl)heptanoic acid

HRID 1639573Notes

Reaction equation

HRID 1639573 reaction equation
C([O:5][C:6](=[O:28])[C:7]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27])([C:15]1[S:19][N:18]=[C:17]([CH3:20])[N:16]=1)C(OC(C)(C)C)=O)(C)(C)C>FC(F)(F)C(O)=O>[C:26]([CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH:7]([C:15]1[S:19][N:18]=[C:17]([CH3:20])[N:16]=1)[C:6]([OH:28])=[O:5])#[N:27]

Participants

3

Reactant 1

HCID 667221752-(5-Cyanopentyl)-2-(3-methyl[1,2,4]thiadiazol-5-yl)malonic acid di-tert-butyl ester

Product 1

HCID 593780557-Cyano-2-(3-methyl[1,2,4]thiadiazol-5-yl)heptanoic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To stirred trifluoroacetic acid (20 mL) was added 2-(5-cyanopentyl)-2-(3-methyl[1,2,4]thiadiazol-5-yl)malonic acid di-tert-butyl ester (2021051) (0.75 g, 1.83 mmol) and the resultant mixture was stirred at room temperature for 1.5 h. The TFA was then removed under reduced pressure, while the temperature of the water bath was maintained below 25° C. The resultant oil was dissolved in dichloromethane (20 mL) and made basic with the careful addition of triethylamine, while keeping the reaction temperature below 20° C. The dichloromethane solution of 7-cyano-2-(3-methyl[1,2,4]thiadiazol-5-yl)heptanoic acid (2021052) was then immediately used in the next step.

Workup

  1. customThe TFA was then removed under reduced pressure, while the temperature of the water bath
  2. temperaturewas maintained below 25° C
  3. dissolutionThe resultant oil was dissolved in dichloromethane (20 mL)
  4. additionmade basic with the careful addition of triethylamine
  5. customthe reaction temperature below 20° C

Sources & evidence

ORD record
ord-e5ce67f66b994123904bfe569262d765
Source dataset
uspto-grants-2012_02
Patent number
US08110577B2

Reaction notes

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