Trimethylsilyldiazomethane → HCID 90712129, compound

HRID 1796870Notes

Reaction equation

HRID 1796870 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[CH:10]([OH:14])[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22][Si](C=[N+]=[N-])(C)C>C1C=CC=CC=1.CO>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)[CH:10]([OH:14])[C:11]([O:13][CH3:22])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 69588616HCID 69588616, compound

Product 1

HCID 90712129HCID 90712129, compound

Reagents, catalysts & solvents 1

HCID 21927730Benzene methanolSolvent

Procedure

A solution of Example 3C (10.234 g, 34 mmol), and trimethylsilyldiazomethane (2.0M in hexanes, 25 mL) in 3.5:1 benzene/methanol (232 mL) at room temperature was stirred at 0° C. for 1 hour, warmed to ambient temperature, stirred for 1 hour, quenched by the dropwise addition of acetic acid, concentrated to provide the desired product. MS (ESI) m/e 316 (M+H)+.

Workup

  1. customquenched by the dropwise addition of acetic acid
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4ba0503749664235a361a5b59115aac1
Source dataset
uspto-grants-2006_04
Patent number
US07030262B2

Reaction notes

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