Triethylamine → HCID 86714596, compound

HRID 1025937Notes

Reaction equation

HRID 1025937 reaction equation
[NH2:1][C:2]([CH3:11])([CH2:6][C:7]([F:10])([F:9])[F:8])[C:3]([OH:5])=[O:4].C(N(CC)CC)C.Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>CO>[CH2:23]([O:22][C:20]([NH:1][C:2]([CH3:11])([CH2:6][C:7]([F:8])([F:9])[F:10])[C:3]([OH:5])=[O:4])=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 83481180HCID 83481180, compound

Product 1

HCID 86714596HCID 86714596, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-amino-4,4,4-trifluoro-2-methylbutanoic acid (255 mg, 1.4 mmol) and triethylamine (800 ul, 4.2 mmol) in MeOH (3 ml) was cooled to 0° C. and benzyl chloroformate (509 mg, 2.98 mmol) was added dropwise. The solution was warmed to RT overnight and concentrated in vacuo. The residue was suspended in EtOAc and extracted with sat. NaHCO3, the aqueous layers acidified with conc. HCl, and the resulting milkly suspension extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford the title compound. LRMS (ESI/APCI, negative): 304 [M−H+].

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with sat. NaHCO3
  3. extractionthe resulting milkly suspension extracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4de07704c0454fda932a6891dae47185
Source dataset
uspto-grants-2014_05
Patent number
US08729112B2

Reaction notes

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