Trimethylsilyldiazomethane → HCID 11548561, compound

HRID 1726010Notes

Reaction equation

HRID 1726010 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[S:22]([NH:25][C:26]2[CH:35]=[CH:34][C:33]3[CH2:32][CH2:31][CH2:30][CH2:29][C:28]=3[C:27]=2[C:36]([OH:38])=[O:37])(=[O:24])=[O:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Si](C=[N+]=[N-])(C)(C)[CH3:40]>C1C=CC=CC=1.CO>[CH3:40][O:37][C:36]([C:27]1[C:28]2[CH2:29][CH2:30][CH2:31][CH2:32][C:33]=2[CH:34]=[CH:35][C:26]=1[NH:25][S:22]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[NH:15][CH2:14][CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]1)(=[O:24])=[O:23])=[O:38]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 68865321HCID 68865321, compound

Product 1

HCID 11548561HCID 11548561, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

A mixture of Example 396 (2.69 g, 5.0 mmol) in benzene (40 mL) and methanol (10 mL) was treated with TMSCHN2 (3.0 mL, 6.0 mmol, 2.0M solution in hexanes). The reaction was stirred at room temperature for 1 hour, then quenched with acetic acid, and diluted with ethyl acetate. The organic layer was washed with aqueous NaHCO3, dried (MgSO4), filtered, concentrated, and purified by column chromatography (25% ethyl acetate/hexanes) to provide the desired product. MS (ESI(+)) m/e 528 (M+H)+.

Workup

  1. customquenched with acetic acid
  2. additiondiluted with ethyl acetate
  3. washThe organic layer was washed with aqueous NaHCO3
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography (25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-84228e1bf7264915b13089f7a0e868bb
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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