Formic Acid → 3-Carboxy-pentanedioic acid di-tert-butyl ester

HRID 2214287Notes

Reaction equation

HRID 2214287 reaction equation
[C:1]([O:5][C:6](=[O:23])[CH2:7][C:8](C(O)=O)([C:17]([OH:19])=[O:18])[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:4])([CH3:3])[CH3:2].C(O)=O>C(OCC)(=O)C>[C:13]([O:12][C:10](=[O:11])[CH2:9][CH:8]([C:17]([OH:19])=[O:18])[CH2:7][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:23])([CH3:14])([CH3:15])[CH3:16]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 87734401HCID 87734401, compound

Product 1

HCID 856474113-Carboxy-pentanedioic acid di-tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

The compound of Example 166 (170 mg, 0.512 mmol) was dissolved in ethyl acetate. Formic acid (61 μL, 1.53 mmol) was added and the mixture was heated at 80° C. for 3 h. After cooling to room temperature, the reaction mixture was extracted three times with water, dried (sodium sulfate), filtered and evaporated to dryness. 1H NMR(CDCl3, 300 MHz): 1.43(s, 18H); 2.50, 2.65(2dd, J1=16.7 Hz, J2=6.2 Hz, 4H); 3.20(p, J=6.2 Hz, 1H).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe reaction mixture was extracted three times with water
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-2683e7632f4e45f0900d55a8d815642a
Source dataset
uspto-grants-2006_09
Patent number
US07105539B2

Reaction notes

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