Sodium Chloride → 4-(15-tert-Butoxycarbonylpentadecanoylamino)benzoic acid methyl ester

HRID 444982Notes

Reaction equation

HRID 444982 reaction equation
[C:1]([O:5][C:6](=[O:24])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=O)([CH3:4])([CH3:3])[CH3:2].ON1C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[NH2:44][C:45]1[CH:54]=[CH:53][C:48]([C:49]([O:51][CH3:52])=[O:50])=[CH:47][CH:46]=1.[Na+].[Cl-]>CN1C(=O)CCC1>[CH3:52][O:51][C:49](=[O:50])[C:48]1[CH:53]=[CH:54][C:45]([NH:44][C:21](=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:24])=[CH:46][CH:47]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 12082Methyl 4-aminobenzoateHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 5781772316-(Tert-butoxy)-16-oxohexadecanoic acid

Product 1

HCID 580794834-(15-tert-Butoxycarbonylpentadecanoylamino)benzoic acid methyl esterYield 42.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
50 °C

Procedure

Hexadecanedioic acid mono-tert-butyl ester (0.4 g, 1.17 mmol) was dissolved in NMP (6 mL). N-Ethyl-N-(3-dimethylaminopropyl)-carbodiimide hydrochloride (0.223 g, 0.1.17 mmol) and 1-hydroxy-7-azabenzotriazole (0.159 g, 1.17 mmol) was added and the mixture was stirred at 50° C. for 1 hour and then allowed to cool to room temperature. Diisopropylethylamin (0.6 mL, 3.5 mmol) was added followed by methyl 4-aminobenzoate (0.353 g, 2.34 mmol). The mixture was stirred overnight under nitrogen at room temperature. The mixture was poured into saturated aqueous NaCl (50 mL), washed with diethylether (3×100 mL between ethyl acetate. The organic phases were collected, dried (Na2SO4) and solvent removed in vacuo. The crude material was purified on silica using ethyl acetate/heptane (50:50), to give pure 4-(15-tert-Butoxycarbonylpentadecanoylamino)benzoic acid methyl ester (235 mg, 42%)

Workup

  1. temperatureto cool to room temperature
  2. stirringThe mixture was stirred overnight under nitrogen at room temperature
  3. washwashed with diethylether (3×100 mL between ethyl acetate
  4. customThe organic phases were collected
  5. dry with materialdried (Na2SO4) and solvent
  6. customremoved in vacuo
  7. customThe crude material was purified on silica

Sources & evidence

ORD record
ord-1bad9b8bcd214cf08ce0e488b69f6a5f
Source dataset
uspto-grants-2013_07
Patent number
US08476228B2

Reaction notes

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