Sodium Hydroxide → HCID 9955064, compound

HRID 1368907Notes

Reaction equation

HRID 1368907 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][CH2:10][CH2:11][C:12]([NH:14][CH2:15][C:16]([NH:18][CH:19]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[N+:31]([O-:33])=[O:32])[CH2:20][C:21]([O:23]C)=[O:22])=[O:17])=[O:13])[CH:3]=1.[OH-].[Na+]>O1CCOCC1>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][CH2:10][CH2:11][C:12]([NH:14][CH2:15][C:16]([NH:18][CH:19]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[N+:31]([O-:33])=[O:32])[CH2:20][C:21]([OH:23])=[O:22])=[O:17])=[O:13])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18517998HCID 18517998, compound

Product 1

HCID 9955064HCID 9955064, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

280 mg of methyl 3-{2-[4-(4-methylpyridin-2-ylamino)butyrylamino]acetylamino}-3-(2-nitrophenyl)propionate (crude material) are dissolved in 30 ml of dioxane, and 0.61 ml of NaOH (2 mol/l) is added. Stirring at room temperature overnight is followed by removal of the solvent by distillation and the usual workup. 3-{2-[4-(4-methylpyridin-2-ylamino)butyrylamino]acetylamino}-3-(2-nitrophenyl)propionic acid is obtained. If an excess of NaOH is used, the sodium salt of 3-{2-[4-(4-methylpyridin-2-ylamino)butyrylamino]acetylamino}-3-(2-nitrophenyl)propionic acid is obtained. Preparative HPLC results in 3-{2-[4-(4-methylpyridin-2-ylamino)butyrylamino]acetylamino}-3-(2-nitrophenyl)propionic acid trifluoroacetate, RT 16.14 min, FAB-MS (M+H)+ 444.

Workup

  1. customis followed by removal of the solvent by distillation

Sources & evidence

ORD record
ord-3e7dbe34a0b94abe83dfdbc08d0c3346
Source dataset
uspto-grants-2003_06
Patent number
US06576637B1

Reaction notes

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