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

HRID 14077Notes

Reaction equation

HRID 14077 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-92306b3288f94584930245ab3ab8e0d5
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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