Stearoyl chloride → HCID 70975496, compound

HRID 2199363Notes

Reaction equation

HRID 2199363 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:30]=[CH:29][CH:28]=[CH:27][C:10]=1[CH:11]=[C:12]1[C:17](=[O:18])[C:16](=[CH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])[CH2:15][NH:14][CH2:13]1.[C:31](Cl)(=[O:49])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48].C(=O)([O-])[O-].[K+].[K+]>ClCCCl>[C:31]([N:14]1[CH2:13][C:12](=[CH:11][C:10]2[CH:27]=[CH:28][CH:29]=[CH:30][C:9]=2[F:8])[C:17](=[O:18])[C:16](=[CH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])[CH2:15]1)(=[O:49])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]

Participants

6

Reactant 4

HCID 8212Stearoyl chlorideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 66993057HCID 66993057, compound2×

Product 1

HCID 70975496HCID 70975496, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Triethylamine (0.4 ml, 2.85 mmol) was added to a solution of compound 1 (300 mg, 0.96 mmol) in ice-cold 1,2 dichloroethane. A solution of stearoyl chloride (450 mg, 1.49 mmol) in 1,2-dichloroethane was added drop-wise to the ice-cold solution of compound 1. The reaction mixture was stirred at room temperature for 16 h. After completion of the reaction, 10% potassium carbonate solution (10 ml) was added, and stirred for 30 min. The organic phase was separated, dried with anhydrous sodium sulfate, and concentrated to obtain a shiny solid of 25 (373 mg, 67% yield). 1H NMR (300 MHz, CDCl3): δ 7.92, 7.89 (2s, 2H, C═CH), 7.50-7.35 (m, 4H, Ar—H), 7.30-7.14 (m, 4H, Ar—H), 4.79, 4.55 (2s, 4H), 2.44 (td, 2H, J=7.3, 2.3), 2.09 (t, 2H, J=7.6), 1.65 (t, 2H, J=7.0), 1.41 (t, 2H, J=7.3), 1.40-1.05 (m, 24H), 0.87 (t, 3H, J=6.7, CH3). 13C NMR (75 MHz, CDCl3): δ 172.05, 133.77, 133.40, 133.48, 130.76, 130.23, 124.29, 116.39, 116.09, 115.81, 46.45, 43.48, 35.26, 33.08, 31.92, 29.69, 29.37, 28.86, 25.06, 24.21, 22.69, 14.12. ESI Mass calculated for C37H50F2NO2(M+H)+578.38. found 578.40.

Workup

  1. additionwas added
  2. stirringstirred for 30 min
  3. customThe organic phase was separated
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-452a21a7cfa04ee1bdb2fc7e30d27dd6
Source dataset
uspto-grants-2016_06
Patent number
US09359196B2

Reaction notes

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