Acetyl chloride → HCID 19377684, compound

HRID 2210887Notes

Reaction equation

HRID 2210887 reaction equation
C(N(CC)CC)C.[NH2:8][CH:9]([C:25]1[N:26]=[N:27][N:28]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[N:29]=1)[C:10]([NH:12][C:13]1[C:18]([CH:19]([CH3:21])[CH3:20])=[CH:17][CH:16]=[CH:15][C:14]=1[CH:22]([CH3:24])[CH3:23])=[O:11].[C:42](Cl)(=[O:44])[CH3:43]>C1COCC1.C(OCC)(=O)C>[CH:22]([C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([CH:19]([CH3:21])[CH3:20])[C:13]=1[NH:12][C:10](=[O:11])[CH:9]([C:25]1[N:26]=[N:27][N:28]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[N:29]=1)[NH:8][C:42](=[O:44])[CH3:43])([CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 19377651HCID 19377651, compound

Product 1

HCID 19377684HCID 19377684, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
24 °C

Procedure

Triethylamine (0.27 g, 2.75 mmol) was added in one portion to a stirred solution of 1.3 g (2.75 mmol) of (±)-N-(2,6-diisopropylphenyl)-2-(2-dodecyl-2H-tetrazol -5-yl)-2-amino-acetamide (prepared as in Example 10) in 50 mL of THF. To the solution was added in one portion 0.23 g (3.0 mmol) of acetyl chloride. The mixture was stirred at 24° C. for 15 minutes, diluted with 50 mL of ethyl acetate, washed with 50 mL of 1N hydrochloric acid, then with 50 mL of 1N sodium hydroxide, brine, and finally dried over MgSO4. The solution was filtered and concentrated by removing the solvents in vacuo to afford an oil. The oil was further purified by chromatography over silica gel (eluting with 1:1 ethyl acetate/hexane) to provide 0.65 g of (±)-N-(2,6-diisopropylphenyl)-2-(2-dodecyl-2H-tetrazol -5-yl)-2-acetylamino-acetamide;

Workup

  1. washwashed with 50 mL of 1N hydrochloric acid
  2. dry with materialwith 50 mL of 1N sodium hydroxide, brine, and finally dried over MgSO4
  3. filtrationThe solution was filtered
  4. concentrationconcentrated
  5. customby removing the solvents in vacuo
  6. customto afford an oil
  7. customThe oil was further purified by chromatography over silica gel (eluting with 1:1 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-840c62abdfdc40dfbe90e4ce7995bf7b
Source dataset
uspto-grants-1995_10
Patent number
US05461049

Reaction notes

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