Diisopropylethylamine → HCID 86603035, compound

HRID 855210Notes

Reaction equation

HRID 855210 reaction equation
[F:1][C:2]([F:13])([F:12])[CH:3]([C:8]([F:11])([F:10])[F:9])[CH2:4][C:5](O)=[O:6].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C.[C:45]([C:49]1[CH:56]=[CH:55][C:52]([CH2:53][NH2:54])=[CH:51][CH:50]=1)([CH3:48])([CH3:47])[CH3:46]>CN(C=O)C.O>[C:45]([C:49]1[CH:50]=[CH:51][C:52]([CH2:53][NH:54][C:5](=[O:6])[CH2:4][CH:3]([C:8]([F:11])([F:10])[F:9])[C:2]([F:13])([F:12])[F:1])=[CH:55][CH:56]=1)([CH3:48])([CH3:46])[CH3:47]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27356554-tert-ButylbenzylamineHCID 27821902(2H-Perfluoro-2-propyl)acetic acid

Product 1

HCID 86603035HCID 86603035, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2.1 g of 4,4,4-trifluoro-3-trifluoromethyl-butyric acid (10 mmol) in 80 ml DMF was treated with 3.12 g of TBTU (10 mmol) and 8.55 ml of N,N-diisopropylethyl amine and stirred for 5 min at rt under argon. Then 1.93 ml of 4-tert-butylbenzylamine (11 mmol) were added and the reaction mixture was stirred 17 h at rt. The reaction mixture was then diluted with 400 ml water and extracted twice with EtOAc, the combined organic phases washed with brine, dried over magnesium sulfate filtered and concentrated in vacuo. The residue was purified by column chromatography (40 g silica gel; heptane/EtOAc 4:1) to give 2.14 g of N-(4-tert-butyl-benzyl)-4,4,4-trifluoro-3-trifluoromethyl-butyramide as a light yellow solid (60%).

Workup

  1. stirringthe reaction mixture was stirred 17 h at rt
  2. extractionextracted twice with EtOAc
  3. washthe combined organic phases washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (40 g silica gel; heptane/EtOAc 4:1)

Sources & evidence

ORD record
ord-d9492f96ec1a40c09a11f21639f6e7ae
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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