Ethyl Acetate → HCID 18469297, compound

HRID 2229820Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[O:13][C:12]([SH:14])=[N:11][C:10]=2[CH:15]=1)=[O:5])[CH3:2].[H-].[Na+].[C:18]([O:22][C:23]([CH2:25][NH:26][CH2:27][CH2:28][CH2:29]Cl)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(OCC)(=O)C>CN(C=O)C>[C:18]([O:22][C:23]([CH2:25][NH:26][CH2:27][CH2:28][CH2:29][S:14][C:12]1[O:13][C:9]2[CH:8]=[CH:7][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:15][C:10]=2[N:11]=1)=[O:24])([CH3:21])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 5-ethoxycarbonyl-2-mercaptobenzoxazole (670 mg) in DMF was added 60% sodium hydride (126 mg) in oil under ice-cooling, and the mixture was stirred for 30 minutes. A solution of 3-tert-butoxycarbonylmethylaminopropyl chloride (623 mg) in DMF was added to the reaction mixture, and the mixture was stirred with heating at 60° C. for 18 hours. Ethyl acetate was added to the reaction mixture, and the organic layer was washed with water and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1 v/v) to give the title compound (594 mg, yield 50%).

Workup

temperaturecooling
stirringthe mixture was stirred
washthe organic layer was washed with water
dry with materialdried over anhydrous sodium sulfate
concentrationThe organic layer was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1 v/v)

Sources & evidence

ORD record: ord-e131adb70ffb4c8fb10ecb63303bd8b6
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06420561B1

Reaction notes

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