Trifluoroacetic acid → HCID 59591077, compound

HRID 2383306Notes

Reaction equation

HRID 2383306 reaction equation
FC(F)(F)C(O)=O.CC(OC([NH:15][CH2:16][CH2:17][C:18]1[C:23]([CH3:24])=[C:22]([O:25][CH3:26])[CH:21]=[CH:20][C:19]=1/[CH:27]=[CH:28]/[C:29]([O:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:30])=O)(C)C>ClCCl>[CH2:32]([O:31][C:29](=[O:30])[CH2:28][CH:27]1[C:19]2[C:18](=[C:23]([CH3:24])[C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH2:17][CH2:16][NH:15]1)[CH2:33][CH2:34][CH3:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59591078HCID 59591078, compound

Product 1

HCID 59591077HCID 59591077, compoundYield 211.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (20.0 ml) was added dropwise to a solution of butyl(2E)-3-[2-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-3-methyl-4-(methyloxy)phenyl]-2-propenoate (Preparation 13; 950 mg, 2.43 mmol) in dichloromethane (20 ml) at 0° C. After 1 h at 0° C., the solvent was removed; purification using a sulphonic acid ion exchange cartridge (SCX; 20 g), eluting with dichloromethane followed by 2N ammonia in methanol, and evaporation of the methanol/ammonia phase gave a brown solid (1.5 g). The solid was triturated with toluene, the mixture filtered, and the mother liquor concentrated in vacuo and dried under vacuum to give the title compound as a brown oil (960 mg).

Workup

  1. customthe solvent was removed
  2. custompurification
  3. washeluting with dichloromethane
  4. customfollowed by 2N ammonia in methanol, and evaporation of the methanol/ammonia phase

Sources & evidence

ORD record
ord-b1e561278f6141b18c03b5e3cad91145
Source dataset
uspto-grants-2012_09
Patent number
US08263620B2

Reaction notes

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