Trimethylsilyldiazomethane → HCID 178448743, compound

HRID 2064510Notes

Reaction equation

HRID 2064510 reaction equation
[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11]([C:13]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:14]=2[CH2:15][N:16]2[CH2:19][CH:18]([C:20]([OH:22])=[O:21])[CH2:17]2)=[O:12])/[N:7]([CH2:31][CH2:32][CH2:33][CH3:34])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[N+](=[CH:37][Si](C)(C)C)=[N-]>CO>[CH2:31]([N:7]1[N:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[S:9]/[C:8]/1=[N:10]\[C:11]([C:13]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:14]=1[CH2:15][N:16]1[CH2:19][CH:18]([C:20]([O:22][CH3:37])=[O:21])[CH2:17]1)=[O:12])[CH2:32][CH2:33][CH3:34]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 178448742HCID 178448742, compound

Product 1

HCID 178448743HCID 178448743, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Example 21A (200 mg, 0.401 mmol) in MeOH was added (diazomethyl)trimethylsilane (1 mL, 2M in ether). The reaction was concentrated to obtain the title compound (170 mg, 0.332 mmol, 83% yield). 1H NMR (300 MHz, CDCl3) δ ppm 0.96-1.04 (m, 3H) 1.35-1.47 (m, 2H) 1.43 (s, 9H) 1.85-1.96 (m, 2H) 3.29-3.50 (m, 3H) 3.54-3.67 (m, 2H) 3.71 (s, 3H) 4.26 (s, 2H) 4.41 (t, J=7.12 Hz, 2H) 7.64-7.79 (m, 2H) 8.48 (s, 1H); (ESI) m/z 513 (M+H)−, 511 (M−H)−.

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-c04d6efb8b8f4e558643e13ba7b0ba55
Source dataset
uspto-grants-2012_10
Patent number
US08288428B2

Reaction notes

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