Triethylamine → HCID 86742995, compound

HRID 1761769Notes

Reaction equation

HRID 1761769 reaction equation
[OH:1][CH2:2]/[CH:3]=[C:4](/[CH3:17])\[CH2:5][CH2:6]/[CH:7]=[C:8](\[CH3:16])/[CH2:9][CH2:10][C:11](=[O:15])[C:12]([CH3:14])=[CH2:13].C([S:21][CH2:22][CH2:23][NH:24][C:25](=[O:27])[CH3:26])(=O)C.C(N(CC)CC)C>CO>[C:25]([NH:24][CH2:23][CH2:22][S:21][CH2:13][CH:12]([CH3:14])[C:11](=[O:15])[CH2:10][CH2:9]/[C:8](/[CH3:16])=[CH:7]/[CH2:6][CH2:5]/[C:4](/[CH3:17])=[CH:3]\[CH2:2][OH:1])(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 14997N,S-DiacetylcysteamineHCID 86742985HCID 86742985, compound

Product 1

HCID 86742995HCID 86742995, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3.5 g (0.0148 mol) of (6E,10Z)-12-hydroxy-2,6,10-trimethyl-1,6,10-dodecatrien-3-one in 110 ml of methanol is treated with 7.15 g of N-(2-acetylthioethyl)acetamide and 6.2 ml of triethylamine. The solution is stirred under argon at room temperature for 24 hours. The solvents are removed on a rotary evaporator. The residue is taken up three times with toluene and freed from solvent on a rotary evaporator. The crude product can be used directly for the acetylation described in Example 12 or can be chromatographed on silica gel with ether-methanol 15:1. After chromatographic purification there is obtained (2Z,6E)-12-[(2-acetamidoethyl)thio]-3,7,11-trimethyl-10-oxo-2,6-dodecadien-1-ol which exhibits the following bands in the IR spectrum: 1737 cm-1, 1715 cm-1, 1437 cm-1, 1366 cm-1, 1277 cm-1,1235 cm-1, 1157 cm-1, 1136 cm-1, 1022 cm-1.

Workup

  1. customThe solvents are removed on a rotary evaporator
  2. customfreed from solvent on a rotary evaporator
  3. customcan be chromatographed on silica gel with ether-methanol 15:1
  4. customAfter chromatographic purification there

Sources & evidence

ORD record
ord-0f90db68ab6240cdbb9c8835422c063a
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

Loading…