Methyl iodide → HCID 86600281, compound

HRID 1441513Notes

Reaction equation

HRID 1441513 reaction equation
Cl.[O:2]1[C@@H:14]2[C@@:15]34[CH2:17][CH2:18][N:19]([CH2:20][CH3:21])[C@@H:9]([C@:10]3([O:23][CH2:24][CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:11][CH2:12][C:13]2=[O:22])[CH2:8][C:7]2=[C:16]4[C:3]1=[C:4]([OH:33])[CH:5]=[CH:6]2.[CH3:34][I:35]>C(#N)C>[I-:35].[O:2]1[C@@H:14]2[C@@:15]34[CH2:17][CH2:18][N@@+:19]([CH2:20][CH3:21])([CH3:34])[C@@H:9]([C@:10]3([O:23][CH2:24][CH2:25][CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:11][CH2:12][C:13]2=[O:22])[CH2:8][C:7]2=[C:16]4[C:3]1=[C:4]([OH:33])[CH:5]=[CH:6]2

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 68537496HCID 68537496, compound

Product 1

HCID 86600281HCID 86600281, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of compound 20 (see Example 20) (250 mg, 0.58 mmol) and methyl iodide (0.36 ml, 5.80 mmol) in acetonitrile (10 ml) was stirred for 6 days at 50° C. (bath temperature) under N2. The solution was evaporated down and the evaporation residue (320 mg of bright beige foamy resin) was purified using column chromatography (silica gel; CH2Cl2/MeOH: each 1 l: (95/5), (92.5/7.5)). Evaporation residue (240 mg, 72%) of amorphous compound 39. Fp. 171-176° C.; IR (KBr): 1723 (C═O) cm−1; 1H-NMR (DMSO-d6): δ 9.55 (s, C3-OH), 7.31-7.16 (m, 5 arom. H), 6.68 (s, 2 arom. H, C1—H, C2—H), 4.87 (s, C5—H), 3.44 (3H, N+CH3, axial), 1.34 (t, 3H, +NCH2CH3, J=7 Hz); MS (CI): m/z 448 (M+).

Workup

  1. customThe solution was evaporated down
  2. customthe evaporation residue (320 mg of bright beige foamy resin) was purified
  3. customEvaporation residue (240 mg, 72%) of amorphous compound 39
  4. custom171-176° C.

Sources & evidence

ORD record
ord-4a218763920243f289dd20fe52acca3d
Source dataset
uspto-grants-2010_02
Patent number
US07655671B2

Reaction notes

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