Sodium Methoxide → HCID 135414274, compound

HRID 2110562Notes

Reaction equation

HRID 2110562 reaction equation
[CH2:1]([C:5]1(C(OC)=O)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[CH:22]=[CH:23][C:24]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[CH:25][C:19]=3[S:18](=[O:32])(=[O:31])[N:17]=2)[C:6]1=[O:33])[CH2:2][CH2:3][CH3:4].C[O-:39].[Na+]>CO>[CH2:1]([C:5]1([OH:39])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[CH:22]=[CH:23][C:24]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])=[CH:25][C:19]=3[S:18](=[O:31])(=[O:32])[N:17]=2)[C:6]1=[O:33])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 136374737HCID 136374737, compound

Product 1

HCID 135414274HCID 135414274, compoundYield 28.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of Example 1G (0.3 g, 0.55 mmol) in 30% weight sodium methoxide in methanol (3 mL) was stirred at 25° C. for 24 h. The solution was quenched with saturated NH4Cl, and extracted with ethyl acetate. The organic extract was concentrated in vacuo, extracted with ethyl acetate, and the organic layer was concentrated in vacuo. Column chromatography on silica (4% methanol/ethyl acetate) afforded the title compound as a white solid (0.095 g, 28.8%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.72 (m, 3H), 0.95-1.29 (m, 5H), 1.63 (m, 2H), 2.99 (s, 3H), 4.95 (s, 1H), 7.17-7.59 (m, 8H), 7.93 (d, J=7.35 Hz, 1H), 9.89 (s, 1H); MS(ESI) m/z 504.1 (M+H)+.

Workup

  1. customThe solution was quenched with saturated NH4Cl
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. concentrationwas concentrated in vacuo
  5. extractionextracted with ethyl acetate
  6. concentrationthe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-5780a1d27d344d2cb29db46108ea0200
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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