Water → N-t-butyl-3-[4-(4-acetyl-8-hydroxytridecyl)benzoyloxy]crotonamide

HRID 26612Notes

Reaction equation

HRID 26612 reaction equation
[C:1]([CH:4]([CH2:17][CH2:18][CH2:19][CH:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:5][CH2:6][CH2:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.[OH2:34].Cl([O-])(=O)(=O)=O.[C:40]([N+:44]1O[C:46]([CH3:49])=[CH:47][CH:48]=1)([CH3:43])([CH3:42])[CH3:41]>C(#N)C>[C:40]([NH:44][C:48](=[O:34])/[CH:47]=[C:46](\[O:13][C:12](=[O:14])[C:11]1[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][CH2:5][CH:4]([C:1](=[O:3])[CH3:2])[CH2:17][CH2:18][CH2:19][CH:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:16][CH:15]=1)/[CH3:49])([CH3:43])([CH3:42])[CH3:41]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 151520Isoxazolium, 2-(1,1-dimethylethyl)-5-methyl-, perchlorate (1:1)HCID 203860504-(4-Acetyl-8-hydroxytridecyl)benzoic acid

Product 1

HCID 70607944N-t-butyl-3-[4-(4-acetyl-8-hydroxytridecyl)benzoyloxy]crotonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(4-acetyl-8-hydroxytridecyl)-benzoic acid (3.62 g., 10 millimole), Example 1, Step F, triethylamine (1.74 ml., 12.5 millimole), and distilled water (18 ml., 1.0 mole) in acetonitrile (100 ml.) is treated with N-t-butyl-5-methylisoxazolium perchlorate (3.0 g., 12.5 millimole). The resulting solution is evaporated in vacuo (water aspirator) at 20°-23° C. for 4 hours providing a tacky residue which is triturated with water (150 ml.) at 0°-5° C. for 15 minutes. After decanting the aqueous phase, the oily residue is dissolved in benzene-ether (1:1) (200 ml.). The organic extract is dried over sodium sulfate, filtered, and evaporated in vacuo at 35°-40° C. providing the desired active ester, N-t-butyl-3-[4-(4-acetyl-8-hydroxytridecyl)benzoyloxy]crotonamide, as a pale yellow oil.

Workup

  1. customThe resulting solution is evaporated in vacuo (water aspirator) at 20°-23° C. for 4 hours
  2. customproviding a tacky residue which
  3. customis triturated with water (150 ml.) at 0°-5° C. for 15 minutes
  4. customAfter decanting the aqueous phase
  5. dissolutionthe oily residue is dissolved in benzene-ether (1:1) (200 ml.)
  6. extractionThe organic extract
  7. dry with materialis dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo at 35°-40° C.

Sources & evidence

ORD record
ord-5d04e62d02d94aa9b71381fccc139435
Source dataset
uspto-grants-1979_04
Patent number
US04150235

Reaction notes

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