Sodium Hydroxide → HCID 22238452, compound

HRID 1743254Notes

Reaction equation

[CH2:1]([C:4]1([C:18]([O:20]C)=[O:19])[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[N:5]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:2]=C.[OH-:22].[Na+]>CO>[OH:22][CH:2]1[CH2:1][C:4]2([N:5]([C:11]([O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[O:12])[C:6]([CH3:10])([CH3:9])[O:7][CH2:8]2)[C:18](=[O:19])[O:20]1

Participants

Conditions

Temperature: 60 °C

Procedure

1.7 g of 3-tert-butyl 4-methyl 4-allyl-2,2-dimethyloxazolidine-3,4-dicarboxylate were dissolved in 20 ml of methanol and 8 ml of 1 N NaOH were added. The mixture was heated at 60° C. for 3 h, allowed to cool, and the methanol was removed in vacuo. The pH of the aqueous phase was adjusted to 2 with 1 N HCl, and it was extracted 3 times with 50 ml of dichloromethane each time. The combined organic phases were dried with MgSO4, and the solvent was removed in vacuo. The residue was taken up in 80 ml of dichloromethane and 10 ml of methanol. The solution was cooled to −78° C., and ozone was passed through until it assumed a pale blue color. Argon was then passed through until the blue color had completely disappeared. 3 ml of dimethyl sulfide were added, and the mixture was allowed to reach room temperature overnight. The solvents were then removed in vacuo. The crude product obtained in this way was employed directly in the next reaction.

Workup

temperatureto cool
customthe methanol was removed in vacuo
extractionwas extracted 3 times with 50 ml of dichloromethane each time
dry with materialThe combined organic phases were dried with MgSO4
customthe solvent was removed in vacuo
temperatureThe solution was cooled to −78° C.
addition3 ml of dimethyl sulfide were added
customThe solvents were then removed in vacuo

Sources & evidence

ORD record: ord-305fa4575643468c9a8889368ff4eb55
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07008957B2

Reaction notes

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