Hydrochloric Acid → HCID 15379243, compound

HRID 1872319Notes

Reaction equation

[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:33](=[O:34])[N:13]3[C:14]([C:26]([O:28]C(C)(C)C)=[O:27])=[C:15]([CH2:18][S:19][C:20]4[N:25]=[CH:24][CH:23]=[CH:22][N:21]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>ClCCl.C1(OC)C=CC=CC=1.O.[Ti](Cl)(Cl)(Cl)Cl>[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:33](=[O:34])[N:13]3[C:14]([C:26]([OH:28])=[O:27])=[C:15]([CH2:18][S:19][C:20]4[N:25]=[CH:24][CH:23]=[CH:22][N:21]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred solution of tert-butyl (6R,7R)-7-phenylacetamido-3-(pyrimidin-2-yl)thiomethyl-ceph-3-em-4-carboxylate (3.5 g, purity 53%, 3.71 mmol) in dichloromethane (150 ml) and anisole (4.65 ml) was cooled to O° C. A solution of titanium tetrachloride (2.3 ml, 21 mmol) in dichloromethane (10 ml) was added. After stirring for 3.5 h at 0° C., the suspension was mixed with a chilled 2 M solution of hydrochloric acid in water. The organic phase was separated and washed with a 1 M solution of hydrochloric acid in water, water, and brine. The organic phase was dried over magnesium sulphate and concentrated to give 2.10 g of (6R,7R)-7-phenylacetamido-3-(pyrimidin-2-yl)thiomethyl-ceph-3-em-4-carboxylic acid (purity 75%, yield 50.9%).

Workup

customThe organic phase was separated
washwashed with a 1 M solution of hydrochloric acid in water, water, and brine
dry with materialThe organic phase was dried over magnesium sulphate
concentrationconcentrated

Sources & evidence

ORD record: ord-b4b35a3b19294a04b9f48781abc3199f
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06107481

Reaction notes

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