Dichloromethane → HCID 18609333, compound

HRID 1788784Notes

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:23]/[O:24][C:25](=[CH2:42])[C:26]([O:28]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:27])/[C:8]([NH:10][CH:11]2[C:14]([CH3:16])([CH3:15])[N:13]([O:17][S:18]([OH:21])(=[O:20])=[O:19])[C:12]2=[O:22])=[O:9])[N:6]=1.C(Cl)Cl.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:23]/[O:24][C:25](=[CH2:42])[C:26]([OH:28])=[O:27])/[C:8]([NH:10][CH:11]2[C:14]([CH3:15])([CH3:16])[N:13]([O:17][S:18]([OH:21])(=[O:19])=[O:20])[C:12]2=[O:22])=[O:9])[N:6]=1

Participants

Conditions

Temperature: -5 °C

Procedure

To the flask containing (±)-(Z)-2-[[[1-(2-amino-4-thiazolyl)-2-[[4,4-dimethyl-2-oxo-1-(sulfooxy)-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-propenoic acid, diphenylmethyl ester was added methylene chloride (10 ml) and anisole (10 ml). After cooling to -5° C., trifluoroacetic acid (8 ml) was added and the reaction mixture was stirred at -5 to 0° C. under argon for 45 minutes. Toluene was added, and the reaction mixture was evaporated to a residue. Water and hexane were added to the residue and the layers were separated. The aqueous layer was adjusted to pH 2.5 with 10% potassium bicarbonate. An HP20 column was run eluting first with water and then an acetone/water gradient. The appropriate fractions were combined and lyophilized to give the title compound as a white solid. 1H-NMR (1:1 D2O/CD3CN) δ1.57 (s, 3H); 1.75 (s, 3H); 5.09 (s, 1H); 5.75 (d, J =2.3 Hz, 1H); 5.86 (d, J2.3 Hz, lH); 7.42 (s, 1H).

Workup

customthe reaction mixture was evaporated to a residue
additionWater and hexane were added to the residue
customthe layers were separated
washAn HP20 column was run eluting first with water

Sources & evidence

ORD record: ord-8c0e7bba371b45db9636a661c316681f
Source dataset: uspto-grants-1987_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04684722

Reaction notes

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