Water → HCID 10870340, compound

HRID 2309577Notes

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:17]/[OH:18])/[C:8]([O:10]CCS(C)(=O)=O)=[O:9])[N:6]=1.Br[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:17]/[O:18][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])/[C:8]([OH:10])=[O:9])[N:6]=1

Participants

Conditions

Temperature: 40 °C

Procedure

In 200 ml of acetone was suspended 10 g (0.0341 mole) of methylsulfonylethyl 2-(2-aminothiazol-4-yl)-(Z)-2-hydroxyiminoacetate as obtained in Example 3. After a serial addition of 9.98 g (0.0512 mole) of t-butyl bromoacetate, 0.6 ml of water and 18.85 g of anhydrous potassium carbonate, the mixture was stirred at 40° C. for 2 hours followed by addition of 200 ml of water. The mixture was stirred at 30°-35° C. for about an hour, whereby the methylsulfonylethyl group was hydrolytically eliminated. Then, the ethyl acetate was added to the hydrolysis reaction mixture. The organic layer was extracted with water and the aqueous layers were combined and adjusted to pH 2 with 2N HCl. The resulting white crystalline precipitate was collected by filtration and dried to give 9.0 g of 2-(2-aminothiazol-4-yl)-(Z)-2-(t-butoxycarbonylmethoxyimino)acetic acid. (Yiled, 87.6%)

Workup

customas obtained in Example 3
stirringThe mixture was stirred at 30°-35° C. for about an hour
extractionThe organic layer was extracted with water
filtrationThe resulting white crystalline precipitate was collected by filtration
customdried

Sources & evidence

ORD record: ord-5c00776934904c36ba2fc0d6bd25770a
Source dataset: uspto-grants-1987_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04695639

Reaction notes

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