Trimethylsilyldiazomethane → HCID 66953071, compound

HRID 723485Notes

Reaction equation

HRID 723485 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([NH:14][C@@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:16])[C@H:10]([C:23]([OH:25])=[O:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Si](C=[N+]=[N-])(C)(C)[CH3:27]>C(Cl)Cl.CO>[C:17]1([C@H:15]([NH:14][C@@H:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][C@H:10]2[C:23]([O:25][CH3:27])=[O:24])[CH3:16])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 66952870HCID 66952870, compound

Product 1

HCID 66953071HCID 66953071, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 261A (280 mg, 0.80 mmol) in 6 mL of 1:1 CH2Cl2/MeOH was added a solution of TMSCHN2 (0.82 ml, 1.64 mmol, 2N in hexane). The mixture was stirred at room temperature for 30 min, then concentrated in vacuo and purified by flash chromatography (hexane/EtOAc: 80:20) on silica gel to give Compound 261B as an oil. It had an analytical HPLC retention time=2.187 min. (Chromolith SpeedROD column 4.5×50 mm, 10–90% aqueous methanol containing 0.1% TFA over 4 min, 4 mL/min, monitoring at 220 nm). Mass (M+1)+=363.

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by flash chromatography (hexane/EtOAc: 80:20) on silica gel

Sources & evidence

ORD record
ord-f3f41dad67ed42b6a07fd5fd74570542
Source dataset
uspto-grants-2006_11
Patent number
US07141571B2

Reaction notes

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