Trimethylsilyldiazomethane → HCID 68549500, compound

HRID 2406864Notes

Reaction equation

HRID 2406864 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[C:17]([CH3:21])[C:18]([OH:20])=[O:19])[CH2:12][CH2:11][CH2:10]2)=[O:5].[CH3:27][Si](C)(C)C=[N+]=[N-]>C(OCC)C>[CH3:27][O:19][C:18](=[O:20])[C:17](=[C:13]1[C:14]2[C:9](=[CH:8][C:7]([NH:6][C:4](=[O:5])[C:3]3[C:2]([F:1])=[CH:25][CH:24]=[CH:23][C:22]=3[F:26])=[CH:16][CH:15]=2)[CH2:10][CH2:11][CH2:12]1)[CH3:21]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 68553980HCID 68553980, compound2×

Product 1

HCID 68549500HCID 68549500, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-[6-(2,6-Difluoro-benzoylamino)-3,4-dihydro-2H-naphthalen-1-ylidene]-propionic acid (Compound 1) (13 mg, 0.036 mmol) was then dissolved in diethylether and excess trimethyl-silyl diazomethane (TMSCHN2) was added at room temperature. After 15 min, the reaction was quenched with acetic acid and concentrated under reduced pressure. The product, 2-[6-(2,6-difluoro-benzoylamino)-3,4-dihydro-2H-naphthalen-1-ylidene]-propionic acid methyl ester (10 mg, 75% yield) was obtained by silica gel chromatography purification using ethyl acetate/hexane as eluent.

Workup

  1. customthe reaction was quenched with acetic acid
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a6e6ea41bbb94c129485c03b6dcfdcab
Source dataset
uspto-grants-2014_08
Patent number
US08809396B2

Reaction notes

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