Trimethylsilyldiazomethane → HCID 178499415, compound

HRID 452997Notes

Reaction equation

HRID 452997 reaction equation
[C:1]([C:5]1[N:9]([CH3:10])[N:8]([CH2:11][C@H:12]2[CH2:16][CH2:15][CH2:14][O:13]2)/[C:7](=[N:17]/[C:18]([C:20]2[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=2[CH2:30][C:31]([OH:33])=[O:32])=[O:19])/[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N+](=[CH:36][Si](C)(C)C)=[N-]>CO>[C:1]([C:5]1[N:9]([CH3:10])[N:8]([CH2:11][C@H:12]2[CH2:16][CH2:15][CH2:14][O:13]2)/[C:7](=[N:17]/[C:18]([C:20]2[CH:25]=[C:24]([C:26]([F:28])([F:29])[F:27])[CH:23]=[CH:22][C:21]=2[CH2:30][C:31]([O:33][CH3:36])=[O:32])=[O:19])/[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 178480267HCID 178480267, compound

Product 1

HCID 178499415HCID 178499415, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of Example 128A (400 mg, 0.856 mmol) in MeOH (3 mL) was added (diazomethyl)trimethylsilane (4.28 ml, 8.56 mmol). The mixture was stirred at 20° C. overnight then concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, gradient 20-100% solvent A in hexane; solvent A=10:1:0.5 ethyl acetate:methanol:triethylamine) to afford the title compound (250 mg, 0.519 mmol, 60.7% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.43 (s, 9H) 1.71-1.85 (m, 3H) 1.99-2.12 (m, 1H) 3.66 (s, 3H) 3.70-3.82 (m, 2H) 3.87 (s, 3H) 4.17-4.23 (m, 1H) 4.25-4.33 (m, 3H) 4.52-4.59 (m, 1H) 6.99 (s, 1H) 7.31 (d, J=7.80 Hz, 1H) 7.52 (dd, J=7.97, 1.53 Hz, 1H) 8.40 (d, J=1.70 Hz, 1H); MS (DCI/NH3) m/z 482 (M+H)+.

Workup

  1. concentrationthen concentrated
  2. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-260e293692414691b588f003b4ebe924
Source dataset
uspto-grants-2013_07
Patent number
US08492371B2

Reaction notes

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