Hexane → methyl O-benzyl-N-(tert-butoxycarbonyl)homoserinate

HRID 348868

Reaction equation

HRID 348868 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C@@H:11]([C:20]([OH:22])=[O:21])[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][Si](C=[N+]=[N-])(C)C.CCCCCC>CO.C1C=CC=CC=1>[CH2:1]([O:8][CH2:9][CH2:10][C@@H:11]([C:20]([O:22][CH3:23])=[O:21])[NH:12][C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 167693TrimethylsilyldiazomethaneHCID 15058464O-Benzyl-N-(tert-butoxycarbonyl)-L-homoserine

Product 1

HCID 54564501methyl O-benzyl-N-(tert-butoxycarbonyl)homoserinate

Reagents, catalysts & solvents 1

HCID 21927730Benzene methanolSolvent

Procedure

To O-benzyl-N-(tert-butoxycarbonyl)homoserine (5.8 g, 18.9 mmol) in 20% methanol/benzene (72 mL) is added 2M trimethylsilyldiazomethane in hexane (12.3 mL, 24.5 mmol), and the reaction stirred at room temperature 1.5 h. The solution is concentrated under reduced pressure to give the title compound in pure form. ESI MS m/z 324.2 [M+H]+.

Workup

  1. concentrationThe solution is concentrated under reduced pressure

Sources & evidence

ORD record
ord-f96bd220ed3f44c9947b29cbacf8e95c
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

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