Methanol → methyl N-(tert-butoxycarbonyl)-4-nitrophenylalaninate

HRID 1861911Notes

Reaction equation

HRID 1861911 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:23](OCC)C.CO.C[Si](C=[N+]=[N-])(C)C>CCCCCC>[CH3:23][O:11][C:10](=[O:12])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 1180712-tert-Butoxycarbonylamino-3-(4-nitro-phenyl)-propionic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 14054107methyl N-(tert-butoxycarbonyl)-4-nitrophenylalaninate

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a mixture of the compound (1.15 g) obtained in Example 63, diethyl ether (6 ml) and methanol (14 ml), a solution of trimethylsilyldiazomethane in n-hexane (2.0 M, 7.4 ml) was added and the resulting mixture was stirred at room temperature for 16 h. The reaction solution was concentrated under reduced pressure to give the titled compound quantitatively.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9fa620512cd443db8e95b83657de6408
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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