Sodium Hydroxide → 1,1-Dimethylethyl 2-[[4-[2-[(carboxymethyl)(2-furanylmethyl)amino]ethyl]phenyl]thio]-2-methyl-propanoate

HRID 353180Notes

Reaction equation

C([O:3][C:4](=[O:32])[CH2:5][N:6]([CH2:26][C:27]1[O:28][CH:29]=[CH:30][CH:31]=1)[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]([CH3:25])([CH3:24])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:11][CH:10]=1)C.[OH-].[Na+]>C(O)C>[C:4]([CH2:5][N:6]([CH2:26][C:27]1[O:28][CH:29]=[CH:30][CH:31]=1)[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([S:15][C:16]([CH3:24])([CH3:25])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:13][CH:14]=1)([OH:32])=[O:3]

Participants

Conditions

Temperature: 80 °C

Procedure

1.0 g of 1,1-dimethylethyl 2-[[4-[2-[(2-ethoxy-2-oxoethyl)(2-furanylmethyl)amino]ethyl]phenyl]thio]-2-methyl-propanoate is treated with 6.5 ml of 1 N NaOH in 10 ml of ethanol. The mixture is stirred at 80° C. for 1 h, concentrated, dissolved in water and acidified with 1 N HCl. Three extractions with ethyl acetate and chromatography (dichloromethane/methanol 5+1) gives 744 mg as a colourless oil.

Workup

concentrationconcentrated
dissolutiondissolved in water
extractionThree extractions with ethyl acetate and chromatography (dichloromethane/methanol 5+1)
customgives 744 mg as a colourless oil

Sources & evidence

ORD record: ord-94434f08a11541ee8b7c19a0d4426925
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06750236B2

Reaction notes

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