Sodium Bicarbonate → HCID 70616087, compound

HRID 1730896Notes

Reaction equation

HRID 1730896 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 6344DichloromethaneSolvent

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 re-extracted 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), λmax. (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 centre of asymmetry is in the side-chain attached to the 7-position). d. 7β-[DL-2-Amino-2(2-naphthyl)acetamido]-3-vinylceph-3-em-4-carboxylic Acid

Workup

  1. extractionThe aqueous phase was re-extracted with methylene chloride (20 ml.)
  2. washthe combined organic phases were washed with water (20 ml.)
  3. customdried

Sources & evidence

ORD record
ord-6a0cab1e384046938c9a97cb1aa2967b
Source dataset
uspto-grants-1976_11
Patent number
US03994884

Reaction notes

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