Ethylamine → HCID 86584735, compound

HRID 1871044Notes

Reaction equation

HRID 1871044 reaction equation
[CH3:1][CH2:2][C@@H:3]([C:5]([O:7][C@@H:8]1[C@@H:13]2[C@@H:14]([CH2:19][CH2:20][C@H:21]3[O:27][C:25](=[O:26])[CH2:24][C@H:23]([OH:28])[CH2:22]3)[C@@H:15]([CH3:18])[CH:16]=[CH:17][C:12]2=[CH:11][C@H:10]([CH3:29])[CH2:9]1)=[O:6])[CH3:4].[CH2:30]([NH2:32])[CH3:31].O1CCCC1>C(OCC)(=O)C>[CH3:1][CH2:2][C@@H:3]([C:5]([O:7][C@@H:8]1[C@@H:13]2[C@@H:14]([CH2:19][CH2:20][C@H:21]3[O:27][C:25](=[O:26])[CH2:24][C@H:23]([OH:28])[CH2:22]3)[C@@H:15]([CH3:18])[CH:16]=[CH:17][C:12]2=[CH:11][C@H:10]([CH3:29])[CH2:9]1)=[O:6])[CH3:4].[CH2:30]([NH-:32])[CH3:31]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 8028TetrahydrofuranHCID 53232Lovastatin

Product 1

HCID 86584735HCID 86584735, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of lovastatin (5.0 g, 0.012 mol) and 2N solution of ethylamine in tetrahydrofuran (37 ml, 0.074 mol) was heated to gentle reflux at 70° C. for 10 hours. The solution was cooled to ambient temperature and ethyl acetate (100 ml) was added; the mixture was washed with 2N hydrochloric acid (3×50 ml). The combined aqueous layers were washed with ethyl acetate (100 ml) and the combined organic layers with water (2×100 ml). The organic layer was dried over sodium sulphate, filtered and evaporated at reduced pressure to give an orange oil.

Workup

  1. temperaturewas heated
  2. temperatureThe solution was cooled to ambient temperature
  3. washthe mixture was washed with 2N hydrochloric acid (3×50 ml)
  4. washThe combined aqueous layers were washed with ethyl acetate (100 ml)
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated at reduced pressure
  8. customto give an orange oil

Sources & evidence

ORD record
ord-d4235a2b5e5c4335bb1f31f392a171a7
Source dataset
uspto-grants-2000_08
Patent number
US06100407

Reaction notes

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