Acetic Acid → HCID 23589629, compound

HRID 1295753Notes

Reaction equation

HRID 1295753 reaction equation
[CH2:1]([C:3]1[C:4]([C:21]([OH:23])=[O:22])=[CH:5][N:6]2[C:11]=1[C:10]([NH:12][C:13]1[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=1)=[N:9][CH:8]=[N:7]2)[CH3:2].[CH3:24][Si](C=[N+]=[N-])(C)C.C(O)(=O)C>CO.C1(C)C=CC=CC=1>[CH3:24][O:22][C:21]([C:4]1[C:3]([CH2:1][CH3:2])=[C:11]2[N:6]([CH:5]=1)[N:7]=[CH:8][N:9]=[C:10]2[NH:12][C:13]1[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=1)=[O:23]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 21945965HCID 21945965, compound

Product 1

HCID 23589629HCID 23589629, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 1140TolueneSolvent

Procedure

To a solution of Example 84 (3 mg, 0.01 mmol) in methanol (0.3 mL) and toluene (0.7 mL) was added trimethylsilyl diazomethane (100 μL of 2.0 M solution in THF). After 30 min. acetic acid and methanol were added and the reaction mixture was concentrated in vacuo. The crude material was purified by chromatography on silica gel eluting with 20% ethyl acetate in hexanes to provide 3 mg of white solid. MS: [M+H]+=328.1; 1H NMR (CDCl3): δ 8.30 (s, 1H), 7.94-7.90 (m, 3H), 7.01 (s, 1H), 6.81 (d, J=8.8 Hz, 1H), 3.96 (s, 3H), 3.88 (s, 3H), 3.32 (q, J=7.6 Hz, 2H), 1.56 (t, J=7.6 Hz, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe crude material was purified by chromatography on silica gel eluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c2227c6692f842ba80861c5871b2c868
Source dataset
uspto-grants-2007_07
Patent number
US07244733B2

Reaction notes

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