2-Methoxyethylamine → HCID 18454788, compound

HRID 1271611Notes

Reaction equation

HRID 1271611 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].[CH3:30][O:31][CH2:32][CH2:33][NH2:34]>O1CCCC1>[CH3:30][O:31][CH2:32][CH2:33][NH:34][C:25](=[O:26])[CH2:24][C@H:23]([OH:28])[CH2:22][C@H:21]([OH:27])[CH2:20][CH2:19][C@@H:14]1[C@@H:13]2[C:12](=[CH:11][C@H:10]([CH3:29])[CH2:9][C@@H:8]2[O:7][C:5](=[O:6])[C@@H:3]([CH3:4])[CH2:2][CH3:1])[CH:17]=[CH:16][C@@H:15]1[CH3:18]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 53232Lovastatin

Product 1

HCID 18454788HCID 18454788, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Lovastatin (50 gm) is mixed with tetrahydrofuran (100 ml) and methoxy ethylamine (140 ml) to obtain a clear solution, the solution is heated to 50° C. and stirred for 4 hours at the same temperature. Then the solvent is distilled off at reduced pressure not allowing the temperature to raise above 50° C., tetrahydrofuran (200 ml) is added to the residue thus obtained, stirred for 30 minutes and distilled off the solvent to give 58 gm of N-methoxyethyl-7-[1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-[[2(S)-methylbutanoyl]oxy]-1(S)-naphthyl]-3(R),5(R)-dihydroxyheptanamide as residue (HPLC Purity 97.3%).

Workup

  1. customto obtain a clear solution
  2. distillationThen the solvent is distilled off at reduced pressure not
  3. temperatureto raise above 50° C.
  4. additiontetrahydrofuran (200 ml) is added to the residue
  5. customthus obtained
  6. stirringstirred for 30 minutes
  7. distillationdistilled off the solvent

Sources & evidence

ORD record
ord-9a3f9974a8454870905ea8179ef5d06c
Source dataset
uspto-grants-2007_04
Patent number
US07205415B2

Reaction notes

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