Pyridine → HCID 86742999, compound

HRID 1761773Notes

Reaction equation

HRID 1761773 reaction equation
[C:1]([NH:4][C@H:5]([C:25]([O:27][CH3:28])=[O:26])[CH2:6][S:7][CH2:8][CH:9]([CH3:24])[C:10](=[O:23])[CH2:11][CH2:12]/[C:13](/[CH3:22])=[CH:14]\[CH2:15][CH2:16]/[C:17](/[CH3:21])=[CH:18]\[CH2:19][OH:20])(=[O:3])[CH3:2].N1C=CC=CC=1.[C:35](OC(=O)C)(=[O:37])[CH3:36]>C(Cl)Cl>[C:1]([NH:4][C@H:5]([C:25]([O:27][CH3:28])=[O:26])[CH2:6][S:7][CH2:8][CH:9]([CH3:24])[C:10](=[O:23])[CH2:11][CH2:12]/[C:13](/[CH3:22])=[CH:14]\[CH2:15][CH2:16]/[C:17](/[CH3:21])=[CH:18]\[CH2:19][O:20][C:35](=[O:37])[CH3:36])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 86743000HCID 86743000, compound

Product 1

HCID 86742999HCID 86742999, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.5 g of methyl N-acetyl-3-[[(6Z,10Z)-12-hydroxy-2,6,10-trimethyl-3-oxo-6,10-dodecadienyl]thio]alaninate dissolved in 15 mil of methylene chloride is treated at 0° with 39 ml of pyridine and 30 ml of acetic anhydride. The solution is stirred at room temperature for 20 hours. After removing the solvent the residue is taken up three times in toluene and freed from solvent each time on a rotary evaporator. The crude product is chromatographed on silica gel with ether-methanol 50:1. There is obtained methyl N-acetyl-3-[[(6Z,10Z)-12-acetoxy-2,6,10-trimethyl-3-oxo-6,10-dodecadienyl]thio]alaninate which exhibits the following absorption bands in the IR spectrum: 1738 cm-1, 1713 cm-1, 1664 cm-1, 1438 cm-1, 1412 cm-1, 1236 cm-1, 1117 cm-1.

Workup

  1. customAfter removing the solvent the residue
  2. customon a rotary evaporator
  3. customThe crude product is chromatographed on silica gel with ether-methanol 50:1

Sources & evidence

ORD record
ord-733b60c8eaf84533a141db7ec57c0259
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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