Sodium Bicarbonate → HCID 70616087, compound

HRID 2420572Notes

Reaction equation

HRID 2420572 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:12][C@@H:13]1[C:29](=[O:30])[N:15]2[C:16]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[C:17]([CH:20]=[CH2:21])[CH2:18][S:19][C@H:14]12.C(=O)([O-])O.[Na+]>C(Cl)Cl.O>[NH2:12][C@@H:13]1[C:29](=[O:30])[N:15]2[C:16]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])=[C:17]([CH:20]=[CH2:21])[CH2:18][S:19][C@H:14]12

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 131710538HCID 131710538, compound

Product 1

HCID 70616087HCID 70616087, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A suspension of t-butyl 7β-amino-3-vinylceph-3-em-4-carboxylate hydrogen p-toluenesulphonate (1.14 g. 2.5 mmole) in methylene chloride was shaken with a solution of sodium hydrogen carbonate (206 mg., 1 equiv.) in water (20 ml.) until the organic layer cleared. The aqueous phase was reextracted with methylene chloride (20 ml.), and the combined organic phases were washed with water (20 ml.), and dried. The solution of t-butyl 7β-amino-3-vinylceph-3-em-4-carboxylate so obtained was stirred and treated with a solution of DL-dicyclohexylcarbodiimide (515 mg., 1 equiv.) in methylene chloride (20 ml.), followed by a solution of Dl-2-t-butoxycarbonylamino-2-(2-naphthyl) acetic acid (753 mg., 1.0 equiv.) in methylene chloride (20 ml.), previously warmed to achieve solution. The reaction mixture was stirred at 23° for 21/2 hours, and the precipitated N,N'-dicyclohexylurea was filtered off. The filtrate was washed with 3%-sodium hydrogen carbonate solution (30 ml.), water (20 ml.), 2N-hydrochloric acid (20 ml.), and water (20 ml.), dried and evaporated to a pale-yellow solid. This solid was triturated with ethyl acetate (160 ml.), the insoluble dicyclohexylurea was removed by filtration, and the filtrate was evaporated to give the title ester as a crystalline solid (1.26 g, 80%), λmax. 288 nm (E1cm 1% 283), γmax. (CHBr3) 3426 (NH), 1780 (azetidin-2-one), 1720 (CO2R), 1708 and 1500 (NH CO2R), 1694 (CONH) and 908 cm-1 (=CH2). The pmr spectrum of the product in CDCl3 showed it to be a 1:1-mixture of the two diastereoisomers (the new center of asymmetry is in the side-chain attached to the 7-position).

Workup

  1. washthe combined organic phases were washed with water (20 ml.)
  2. customdried

Sources & evidence

ORD record
ord-e29f984a5aed45a4afd395126f57be8f
Source dataset
uspto-grants-1978_08
Patent number
US04110534

Reaction notes

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