Lithium Hydroxide → HCID 67148381, compound

HRID 2427927Notes

Reaction equation

HRID 2427927 reaction equation
[OH-].[Li+].[CH3:3][O:4][C:5]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([CH2:13][C:14]([O:16]C)=[O:15])=[C:7]([CH2:18][N:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20]([CH3:22])=[O:21])[CH:6]=1>CO>[CH3:3][O:4][C:5]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([CH2:13][C:14]([OH:16])=[O:15])=[C:7]([CH2:18][N:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20]([CH3:22])=[O:21])[CH:6]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67148503HCID 67148503, compound

Product 1

HCID 67148381HCID 67148381, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous solution of lithium hydroxide (0.5 M, 56 ml, 28 mmol) was added to a solution of methyl 4,5-dimethoxy-2-[(phenylacetamino)methyl]phenylacetate 6 (2 g, 5.6 mmol) in methanol (50 ml). The reaction mixture was stirred at ambient temperature for 12 hours, then neutralized with an aqueous solution of HCl (2N) and precipitation of the product was observed. Filtration gave the 4,5-dimethoxy-2-[(phenylacetamino)methyl]-phenylacetic acid 7 (1.5 g, 78%) in the form of a white powder. M.p.=186° C. 1H NMR ((CD3)2SO, 300 MHz) δ 8.40 (br s, 1H), 7.30-7.20 (m, 6H), 6.80 (s, 1H), 6.73 (s, 1H), 4.18 (d, J=5.6 Hz, 2H), 3.70 (s, 3H), 3.59 (s, 3H), 3.55 (s, 2H), 3.44 (s, 2H). 13C NMR ((CD3)2SO, 75 MHz) δ 172.8, 170.0, 147.4, 147.3, 136.6, 129.9, 129.0 (2C), 128.3 (2C), 126.4, 125.2, 114.6, 111.9, 55.6, 55.4, 42.5, 39.6, 37.5. Analysis calculated for C19H21NO5: C=66.46, H=6.16 and N=4.08. Analysis measured: C=66.52, H=5.92 and N=4.06.

Workup

  1. customneutralized with an aqueous solution of HCl (2N) and precipitation of the product
  2. filtrationFiltration

Sources & evidence

ORD record
ord-332aa2d882b14361a2ba9530cb4d114f
Source dataset
uspto-grants-2011_06
Patent number
US07968735B2

Reaction notes

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