Stearoyl chloride → HCID 58526181, compound

HRID 1184983Notes

Reaction equation

HRID 1184983 reaction equation
[CH:1]1([NH:7][C:8]([O:16][N:17]2[C:22]([CH3:24])([CH3:23])[CH2:21][CH:20]([O:25][C:26](=[O:28])[CH3:27])[CH2:19][C:18]2([CH3:30])[CH3:29])=[N:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:38](Cl)(=[O:56])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]>C1(C)C=CC=CC=1>[CH:10]1([N:9]([C:38](=[O:56])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[C:8]([O:16][N:17]2[C:18]([CH3:30])([CH3:29])[CH2:19][CH:20]([O:25][C:26](=[O:28])[CH3:27])[CH2:21][C:22]2([CH3:24])[CH3:23])=[N:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 8212Stearoyl chloride2×HCID 8471Triethylamine2×HCID 58526184HCID 58526184, compound

Product 1

HCID 58526181HCID 58526181, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of compound 1 (4.21 g, 10 mmol) [prepared according to Example 1] in toluene (25 ml) is added triethylamine (1.46 ml, 10.5 mmol) and stearoyl chloride (3.2 g, 10.5 mmol). The mixture is stirred at room temperature for 30 minutes and then additional triethylamine (1.46 ml, 10.5 mmol) and stearoyl chloride (3.2 g, 10.5 mmol) is added. The suspension is stirred at room temperature for 18 hours, then evaporated and chromatographed over silica gel with hexane-ethyl acetate (9:1) to afford 4.03 g of the title compound as a colorless oil.

Workup

  1. stirringThe suspension is stirred at room temperature for 18 hours
  2. customevaporated
  3. customchromatographed over silica gel with hexane-ethyl acetate (9:1)

Sources & evidence

ORD record
ord-1da6d11a40824aabbf2266f3a250a24f
Source dataset
uspto-grants-2014_03
Patent number
US08669398B2

Reaction notes

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