Tributylamine → 4-[(2R, 3S)-3-methoxy-2-methylbutyryloxy]phenyl 4'-octyloxy-4-biphenylcarboxylate

HRID 2253567Notes

Reaction equation

HRID 2253567 reaction equation
[CH3:1][O:2][C@@H:3]([CH3:9])[C@@H:4]([CH3:8])[C:5]([OH:7])=[O:6].[CH2:10]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([O:33][C:34]3[CH:39]=[CH:38][C:37](O)=[CH:36][CH:35]=3)=[O:32])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(N(CCCC)CCCC)CCC.[I-].ClC1C=CC=C[N+]=1C>O1CCCC1>[CH2:10]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:26]=[CH:27][C:28]([C:31]([O:33][C:34]3[CH:39]=[CH:38][C:37]([O:6][C:5](=[O:7])[C@H:4]([CH3:8])[C@@H:3]([O:2][CH3:1])[CH3:9])=[CH:36][CH:35]=3)=[O:32])=[CH:29][CH:30]=2)=[CH:21][CH:20]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 7622TributylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 189528864-Hydroxyphenyl 4'-octyloxy-4-biphenylcarboxylateHCID 55300075(2R, 3S)-3-methoxy-2-methylbutyric acid

Product 1

HCID 150657044-[(2R, 3S)-3-methoxy-2-methylbutyryloxy]phenyl 4'-octyloxy-4-biphenylcarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2R, 3S)-3-methoxy-2-methylbutyric acid prepared in the above i) (0.79 g), 4-hydroxyphenyl 4'-octyloxy-4-biphenylcarboxylate (2.5 g) and tributylamine (2.66 g) were dissolved in dehydrated tetrahydrofuran (40 ml) and 2-chloro-1-methylpyridinium iodide (1.84 g) was added thereto. The mixture was heated under reflux for 7 hours. Insoluble materials were filtered off and the filtrate was concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography [eluent:chloroform:n-hexane (4:1)] and recrystallized from ethanol to obtain the title compound (0.36 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 7 hours
  3. filtrationInsoluble materials were filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified by silica gel column chromatography [eluent:chloroform:n-hexane (4:1)]
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-00a367f2ebe1432e8dfc62292fe1e693
Source dataset
uspto-grants-1993_08
Patent number
US05232853

Reaction notes

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