Anisole → 6,7-Bis(palmitoyloxy)-4-thiaheptanoic acid

HRID 1720788Notes

Reaction equation

HRID 1720788 reaction equation
COC1C=CC(C[O:8][C:9](=[O:52])[CH2:10][CH2:11][S:12][CH2:13][CH:14]([O:34][C:35](=[O:51])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[CH2:15][O:16][C:17](=[O:33])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=CC=1.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[C:35]([O:34][CH:14]([CH2:15][O:16][C:17](=[O:33])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:13][S:12][CH2:11][CH2:10][C:9]([OH:52])=[O:8])(=[O:51])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50]

Participants

4

Reactant 2

HCID 7519AnisoleHCID 106052466,7-Bis(palmitoyloxy)-4-thiaheptanoic acid p-methoxybenzyl ester

Product 1

HCID 105562786,7-Bis(palmitoyloxy)-4-thiaheptanoic acidYield 65%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To 6,7-bis(palmitoyloxy)-4-thiaheptanoic acid p-methoxybenzyl ester as obtained in Reference Example 3 (1.17 g), a solution of anisole (0.33 ml) in trifiuoroacetic acid (3.3 ml) was added at room temperature, followed by stirring at room temperature for 30 minutes. The reaction mixture was concentrated, and the residue was washed with hexane to yield the title compound (643 mg, yield 65%) as a powder.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washthe residue was washed with hexane

Sources & evidence

ORD record
ord-4974e02e44bc46a58437aa746abfdd4a
Source dataset
uspto-grants-1996_04
Patent number
US05506267

Reaction notes

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