Pyridine → HCID 70509313, compound

HRID 1702712Notes

Reaction equation

HRID 1702712 reaction equation
[OH:1][CH:2]1[C@@H:6]2[CH2:7][C:8](=[O:9])[N:5]2[CH:4]([C:10]([O:12][CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH:3]1[CH3:26].C(Cl)Cl.N1C=CC=CC=1.[C:36](OC(=O)C)(=[O:38])[CH3:37]>CN(C)C1C=CN=CC=1.C(OCC)(=O)C.C(Cl)(Cl)Cl>[C:36]([O:1][CH:2]1[C@@H:6]2[CH2:7][C:8](=[O:9])[N:5]2[CH:4]([C:10]([O:12][CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11])[CH:3]1[CH3:26])(=[O:38])[CH3:37]

Participants

8

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 70507453HCID 70507453, compound

Product 1

HCID 70509313HCID 70509313, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

Freshly prepared benzhydryl 1-hydroxy-2-methylcarbapenam-3-carboxylate (53 mg., 0.15 mmoles) was dissolved in 5 ml. of methylene chloride and cooled to -10° C. Pyridine (12 mg., 0.15 mmoles), acetic anhydride (15.4 mg., 0.15 mmoles) and 4-dimethylaminopyridine (18.4 mg., 0.15 mmoles) were added and the mixture stirred for 1 hour at -10° C., at which time tlc (4:1 chloroform:ethyl acetate) indicated clean conversion to the acetate ester. The reaction mixture was chromatographed on silicia gel (9:1 methylene chloride:ethyl acetate eluant), yielding purified benzhydryl 1-acetoxy-2-methylcarbapenam-3-carboxylate [Rf 0.65 (4:1 chloroform:ethyl acetate)].

Workup

  1. customThe reaction mixture was chromatographed on silicia gel (9:1 methylene chloride:ethyl acetate eluant)
  2. customyielding
  3. custompurified benzhydryl 1-acetoxy-2-methylcarbapenam-3-carboxylate [Rf 0.65 (4:1 chloroform:ethyl acetate)]

Sources & evidence

ORD record
ord-725b099a25834c3c9d3afea99e0a7d51
Source dataset
uspto-grants-1982_09
Patent number
US04348264

Reaction notes

Loading…