Triethylamine → tert-Butyl 3-(4-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-1,3-oxazol-5-yl)propanoate

HRID 534969Notes

Reaction equation

HRID 534969 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].[C:19]([O:23][C:24](=[O:35])[CH2:25][CH2:26][C:27]1[O:31][CH:30]=[N:29][C:28]=1[C:32](O)=[O:33])([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CC#N>[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([C:32]([C:28]2[N:29]=[CH:30][O:31][C:27]=2[CH2:26][CH2:25][C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:35])=[O:33])[CH2:15][CH2:14]1)([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 667509145-(3-tert-Butoxy-3-oxopropyl)-1,3-oxazole-4-carboxylic acidHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 66792852tert-Butyl 3-(4-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-1,3-oxazol-5-yl)propanoateYield 84.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride (Reference Example 1, 2.18 g, 7.50 mmol), 5-(3-tert-butoxy-3-oxopropyl)-1,3-oxazole-4-carboxylic acid (Reference Example 22, 1.90 g, 7.88 mmol), triethylamine (1.52 g, 7.88 mmol), EDCI (1.51 g, 7.88 mmol) and HOBt (1.21 g, 7.88 mmol) in MeCN (40 mL) was stirred at room temperature for 16 h. The reaction mixture was concentrated under reduced pressure, and the resulting residue was partitioned between ethyl acetate and water. The organic layer was washed with 10% NaHCO3, saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (silica gel, 9:1-2:3 hexane/ethyl acetate) to give the title compound (2.81 g) as a light yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with 10% NaHCO3, saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by flash column chromatography (silica gel, 9:1-2:3 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-cdab737270c4451eb02b19fc85c1820b
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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