Hydrochloric Acid → HCID 11068306, compound

HRID 1872314Notes

Reaction equation

HRID 1872314 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:21]([O:23]CC4C=CC(OC)=CC=4)=[O:22])=[C:15]([CH:18]=[CH:19][CH3:20])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>ClCCl.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:21]([OH:23])=[O:22])=[C:15](/[CH:18]=[CH:19]/[CH3:20])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 54420568HCID 54420568, compound

Product 1

HCID 11068306HCID 11068306, compoundYield 10.2%

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 4-methoxybenzyl (6-R,7R)-7-phenylacetamido-3-(1-propenyl)-ceph-3-em-4-carboxylate (0.509 g, purity 9% E-isomer, 84% Z-isomer, 0.99 mmol) in dichloromethane (15 ml) was cooled to 2° C. Titanium tetrachloride (0.5 ml, 4.5 mmol) was added in 1 min. After 30 min the brown suspension was mixed with a chilled mixture of dichloromethane (50 ml) and a 2 M solution of hydrochloric acid in water (50 ml). The organic phase was separated and extracted with a 2 M solution of hydrochloric acid in water (3×50 ml) The aqueous phases were extracted with dichloromethane (25 ml). The combined organic phases were analyzed using HPLC: 0.036 g (6R,7R)-7-phenylacetamido-3-[(E)-1-propenyl]-ceph-3-em-4-carboxylic acid (0.10 mmol, yield 10.2%); 0.301 g (6R,7R)-7-phenylacetamido-3-[(Z)-1-propenyl]-ceph-3-em-4-carboxylic acid (0.84 mmol, yield 84.8%). The overall yield is therefore 95.0%.

Workup

  1. customThe organic phase was separated
  2. extractionextracted with a 2 M solution of hydrochloric acid in water (3×50 ml) The aqueous phases
  3. extractionwere extracted with dichloromethane (25 ml)

Sources & evidence

ORD record
ord-ef1e8bd400d9459a8c3b432495f4c1ce
Source dataset
uspto-grants-2000_08
Patent number
US06107481

Reaction notes

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