Methacryloyl chloride → N-(2-Methylacryloyl)-L-glutamic acid

HRID 978178Notes

Reaction equation

[Na+].[NH2:2][C@H:3]([C:9]([O-:11])=[O:10])[CH2:4][CH2:5][C:6]([OH:8])=[O:7].[OH-].[Na+].[C:14](Cl)(=[O:18])[C:15]([CH3:17])=[CH2:16]>>[C:14]([NH:2][C@H:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][C:6]([OH:8])=[O:7])(=[O:18])[C:15]([CH3:17])=[CH2:16]

Participants

Reactant 3

HCID 13528Methacryloyl chloride

HCID 14798Sodium Hydroxide

HCID 23672308Sodium Glutamate

Product 1

HCID 18595884N-(2-Methylacryloyl)-L-glutamic acidYield 48.7%

Procedure

The same procedure as described in Example A is utilized with 100 g (0.6 mol) of L-glutamic acid monosodium salt, 50 g (0.125 mol) of sodium hydroxide, and 63 g of methacryloyl chloride to yield 62 g (48.7%) of a crystalline material, melting point 128°-130° C. NMR (D2O), 5.7 gamma (s, 1H, =CH2), 5.4 gamma (s, 1H, =CH2), 4.4 gamma (2 d, 1H, CH), 2.0-2.7 gamma (m, 4H, CH2CH2), and 1.9 gamma (s, 3H, CH3).

Sources & evidence

ORD record: ord-e18ec757710444558ffe22b6ceddc88d
Source dataset: uspto-grants-1987_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04663409

Reaction notes

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