Trimethylsilyldiazomethane → HCID 66972826, compound

HRID 1367826Notes

Reaction equation

HRID 1367826 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][S:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22][Si](C=[N+]=[N-])(C)C>CO.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][S:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[C:10]([O:12][CH3:22])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 66972798HCID 66972798, compound

Product 1

HCID 66972826HCID 66972826, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To 2(S)-tert-butoxycarbonylamino-4-(pyridin-2-ylsulfanyl)butyric acid (0.75 g, 2.40 mmol) in methanol (16 mL) and toluene (50 mL) was added a 2.0M solution of (trimethylsilyl)diazomethane (3.12 mmol) dropwise. After 3 h, the reaction mixture was concentrated to give methyl 2(S)-tert-butoxycarbonylamino-4-(pyridin-2-ylsulfanyl)butyrate as an oily residue which was used without further purification.

Workup

  1. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-04a8ee936aa2461f9e4d7d2fa9d81438
Source dataset
uspto-grants-2011_02
Patent number
US07893093B2

Reaction notes

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