Triethylamine → HCID 86598934, compound

HRID 2251574Notes

Reaction equation

HRID 2251574 reaction equation
[CH3:1][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)=[CH:12][CH:11]=1)([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:30]([N:32](CC)CC)C.N#CBr>ClCCl>[C:30]([N:18]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:24][CH:25]=1)[CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][C:2]([CH3:1])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:11][CH:12]=1)#[N:32]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 10476Cyanogen Bromide2×HCID 59643115HCID 59643115, compound

Product 1

HCID 86598934HCID 86598934, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of ethyl 2-methyl-2-[4-(2-{[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]propanoate (12 g; 29.34 mmol) and triethylamine (4.5 ml; 32.27 mmol) in 100 ml of dichloromethane was treated under nitrogen with cyanogen bromide (10.3 ml of a 3M solution in dichloromethane; 30.9 mmol). After 1.5 hr, additional triethylamine (2 ml) and cyanogen bromide (2.5 ml) were added and stirred another 30 minutes. The reaction mixture was concentrated and the residue partitioned between ethyl acetate and water. The organic phase was washed with water (three times) and brine, dried over sodium sulfate and concentrated. Purification by flash chromatography using ethyl acetate-hexane mixtures (5–40% gradient) afforded ethyl 2-[4-(2-{cyano[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (10.9 g; 85% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic phase was washed with water (three times) and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification by flash chromatography

Sources & evidence

ORD record
ord-4d13c0bd2bb749ef830b6fa5e4b8a2c4
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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