Potassium Hydroxide → (S)-2-[3-(6-Hydroxy-naphthalen-1-yl)-ureido]-pentanedioic acid 5-tert-butyl ester

HRID 581691Notes

Reaction equation

C[O:2][C:3](=[O:29])[C@@H:4]([NH:14][C:15]([NH:17][C:18]1[C:27]2[C:22](=[CH:23][C:24]([OH:28])=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)=[O:16])[CH2:5][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[OH-].[K+]>O>[C:10]([O:9][C:7](=[O:8])[CH2:6][CH2:5][C@H:4]([NH:14][C:15]([NH:17][C:18]1[C:27]2[C:22](=[CH:23][C:24]([OH:28])=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)=[O:16])[C:3]([OH:29])=[O:2])([CH3:13])([CH3:11])[CH3:12]

Participants

Conditions

Temperature: 50 °C

Procedure

To the methyl ester from Step 1 above (5 mmol, 2.0 g) was added potassium hydroxide (5 mmol, 0.28 g) in water (7 mL), and heated at 50° C. After stirring for 36 hours, the reaction mixture was evaporated to dryness, the residue was dissolved in water (15 mL), acidified to pH≈5 using 0.50 N hydrochloric acid, extracted with the ethyl acetate (4×50 mL), and dried to provide product as a light brown oil (1.20 g, 62%).

Workup

customthe reaction mixture was evaporated to dryness
dissolutionthe residue was dissolved in water (15 mL)
extractionextracted with the ethyl acetate (4×50 mL)
customdried

Sources & evidence

ORD record: ord-931732869abd47dbab78f8621323e93f
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05922697

Reaction notes

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