Hydrochloric Acid → HCID 11056668, compound

HRID 582247Notes

Reaction equation

HRID 582247 reaction equation
[CH2:1]=[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][CH2:3]1.Cl>ClCCl.O.[Ti](Cl)(Cl)(Cl)Cl>[CH2:1]=[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][CH2:3]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 10872795HCID 10872795, compound

Product 1

HCID 11056668HCID 11056668, compoundYield 60.2%

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of tert-butyl (4R, 6R, 7R) -3-methylene-7-phenylacetamido-cepham-4-carboxylate (0.83 g, purity 93.7%, 2.0 mmol) in dichloromethane (80 ml) was cooled to 0° C. Titanium tetrachloride (0.66 ml, 6.0 mmol) was added in 1 min. After stirring for 4 h at 0° C., the suspension was mixed with a chilled 2M solution of hydrochloric acid in water (40 ml). The organic phase was separated and washed with a 1M solution of hydrochloric acid in water (20 ml), water (20 ml), and brine (20 ml). The organic phase was dried over magnesium sulphate and evaporated to give 0.40 g of (4R,6R,7R)-3-methylene-7-phenylacetamido-cepham-4-carboxylic acid (purity 75%, yield 45.1%).

Workup

  1. customThe organic phase was separated
  2. washwashed with a 1M solution of hydrochloric acid in water (20 ml), water (20 ml), and brine (20 ml)
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-eb75550bb1544dd9a16f2907b88afb68
Source dataset
uspto-grants-1999_07
Patent number
US05922861

Reaction notes

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