Tetrahydrofuran → HCID 19906417, compound

HRID 2371807Notes

Reaction equation

HRID 2371807 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[C:14]2[CH2:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=2[O:28][CH3:29])=[CH:9][CH:8]=1)(O)=[O:2].O1CCCC1.ClC(OCC(C)C)=O.[CH2:43]([N:45](CC)[CH2:46]C)C>>[CH3:43][N:45]([CH3:46])[C:1]([CH2:4][CH2:5][CH2:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[C:14]2[CH2:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=2[O:28][CH3:29])=[CH:9][CH:8]=1)=[O:2]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 19906359HCID 19906359, compound

Product 1

HCID 19906417HCID 19906417, compoundYield 43%

Procedure

To a mixture of methyl 4-[7-(3-carboxypropyl)-naphth-1-ylmethyl]-3-methoxybenzoate (2.40 g), tetrahydrofuran (70 ml) and triethylamine (0.681 g) was added isobutyl chloroformate (0.87 ml) After stirring for 30 min, dimethylamine (2.0 g) was bubbled into the solution and stirring continued for 18 h. The reaction mixture was partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was washed (1N hydrochloric acid, aqueous sodium bicarbonate (5% w/w), brine) and dried (MgSO4). Evaporation and flash chromatography, eluting with ethyl acetate:methylene chloride (0:1, 1:10 and 2:10, successively), to give methyl 4-[7-(3-dimethylcarbamoylpropyl)naphth-1-ylmethyl]-3-methoxybenzoate (1.10 g, 43%) as a glassy solid; MS(CI), m/e=419(M+H).

Workup

  1. customdimethylamine (2.0 g) was bubbled into the solution
  2. stirringstirring
  3. waitcontinued for 18 h
  4. customThe reaction mixture was partitioned between ethyl acetate and 1N hydrochloric acid
  5. washThe organic layer was washed (1N hydrochloric acid, aqueous sodium bicarbonate (5% w/w), brine)
  6. dry with materialdried (MgSO4)
  7. customEvaporation and flash chromatography
  8. washeluting with ethyl acetate:methylene chloride (0:1, 1:10 and 2:10

Sources & evidence

ORD record
ord-0179f308b4db4a078fa4b3b8690636b2
Source dataset
uspto-grants-1992_03
Patent number
US05095038

Reaction notes

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