Sodium Hydroxide → 3-Methyl-2-{2-oxo-3-(4-(pyridin-4-ylmethoxy)benzyl)imidazolidin-1-yl}-butyric acid

HRID 1994306Notes

Reaction equation

[CH3:1][CH:2]([CH3:30])[CH:3]([N:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)[C:10]1=[O:29])[C:4]([O:6]CC)=[O:5].[OH-].[Na+]>CO>[CH3:1][CH:2]([CH3:30])[CH:3]([N:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)[C:10]1=[O:29])[C:4]([OH:6])=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl 3-methyl-2-{2-oxo-3-(4-(pyridin-4-ylmethoxy)benzyl)imidazolidin-1-yl}-butyrate (45 mg; 0.11 mmol) was dissolved in methanol (1.5 ml) and cooled to 0° C. NaOH (1N, 5 ml) was added, and the mixture was allowed to warm to RT over the course of 3 h. The methanol was then removed under reduced pressure, and water (1.5 ml) and saturated NaH2PO4 solution (3 ml) were added to the residue. The solid was filtered off with suction and washed with water. Drying under reduced pressure at 60° C. resulted in 3-methyl-2-{2-oxo-3-(4-(pyridin-4-ylmethoxy)benzyl)imidazolidin-1-yl}-butyric acid (36 mg; 0.09 mmol). MS: 384.45 (M+H); Rt: 0.87 min (method: gradient 0 min 96% H2O (0.05% TFA) 2.0 min 95% acetonitrile, 95% acetonitrile to 2.4 min, 4% acetonitrile 2.45 min; flow rate 1 ml/min; column 0.4 μL (YMC J'sphere ODS H80 20X2 1.4μ); 30° C.)

Workup

temperatureto warm to RT over the course of 3 h
customThe methanol was then removed under reduced pressure, and water (1.5 ml) and saturated NaH2PO4 solution (3 ml)
additionwere added to the residue
filtrationThe solid was filtered off with suction
washwashed with water
customDrying under reduced pressure at 60° C.

Sources & evidence

ORD record: ord-34232875446548ccbef6be08589f5b58
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652143B2

Reaction notes

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