Hydrochloric Acid → HCID 15379245, compound

HRID 1872312Notes

Reaction equation

HRID 1872312 reaction equation
[CH3:1][C:2]1[C@H:7]([C:8]([O:10]C(C)(C)C)=[O:9])[N:6]2[C:15](=[O:27])[C@@H:16]([NH:17][C:18](=[O:26])[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C@H:5]2[S:4][CH:3]=1.Cl>ClCCl.O.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][C:2]1[C@H:7]([C:8]([OH:10])=[O:9])[N:6]2[C:15](=[O:27])[C@@H:16]([NH:17][C:18](=[O:26])[CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C@H:5]2[S:4][CH:3]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 15379244HCID 15379244, compound

Product 1

HCID 15379245HCID 15379245, compoundYield 82.7%

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of tert-butyl (4R,6R,7R)-3-methyl-7-phenylacetamido-ceph-2-em-4-carboxylate (0.776 g, 2.0 mmol) in dichloromethane (30 ml) was cooled to 0° C. Titanium tetrachloride (0.6 ml, 5.5 mmol) was added in 1 min. After stirring for 2.5 h at 0° C., the suspension was mixed with a chilled 2 M solution of hydrochloric acid in water (40 ml). The organic phase was separated and washed with a 1 M solution of hydrochloric acid in water (20 ml), water (20 ml), and brine (20 ml). The organic phase was concentrated to give 0.55 g of (4R,6R,7R)-3-methyl-7-phenylacetamido-ceph-2-em-4-carboxylic acid (yield 82.7%).

Workup

  1. customThe organic phase was separated
  2. washwashed with a 1 M solution of hydrochloric acid in water (20 ml), water (20 ml), and brine (20 ml)
  3. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-c2121715911743e0aa43a1e8740630fa
Source dataset
uspto-grants-2000_08
Patent number
US06107481

Reaction notes

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