Hydrochloric Acid → HCID 10075662, compound

HRID 1707494Notes

Reaction equation

HRID 1707494 reaction equation
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:63])[C@@H:24]([NH:25][C:26](=[O:62])/[C:27](/[C:49]4[N:50]=[C:51]([NH:54]C(OC(C)(C)C)=O)[S:52][CH:53]=4)=[N:28]\[O:29]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C@H:21]3[S:20][CH2:19][C:18]=2[S:64][CH2:65][S:66][C:67]2[N:68]=[N:69][N:70]([CH3:72])[N:71]=2)=[O:16])C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1(OC)C=CC=CC=1.[N+](C)([O-])=O.O>[NH2:54][C:51]1[S:52][CH:53]=[C:49](/[C:27](=[N:28]/[OH:29])/[C:26]([NH:25][C@@H:24]2[C:23](=[O:63])[N:22]3[C:17]([C:15]([OH:16])=[O:14])=[C:18]([S:64][CH2:65][S:66][C:67]4[N:68]=[N:69][N:70]([CH3:72])[N:71]=4)[CH2:19][S:20][C@H:21]23)=[O:62])[N:50]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 10102568HCID 10102568, compound

Product 1

HCID 10075662HCID 10075662, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6375NitromethaneSolventHCID 7519AnisoleSolvent2×

Procedure

To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetylamino]-3-(2-methyltetrazol-5-ylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester (1.16 g: 1.12 mMol.) in a mixture of anisole (4 ml) and nitromethane (16 ml) at -40° C. is added a solution of aluminum chloride (1.19 g: 8.95 mMol.) in anisole (4 ml), and the mixture is stirred at -30° to -40° C. for 1 hour. The reaction mixture is mixed with 1N-hydrochloric acid (9 ml), diluted with water, washed with ethyl acetate, concentrated to remove the remaining organic solvents, and passed through a column of styrene-divinylbenzene copolymer adsorbent. The adsorbed material is eluted with water-methanol (1:4) and concentrated to give powder which is washed with ethyl acetate to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-(2-methyltetrazol-5-ylthiomethylthio)-3-cephem-4-carboxylic acid (466 mg) as yellow powder. Yield: 79%.

Workup

  1. washwashed with ethyl acetate
  2. concentrationconcentrated
  3. customto remove the remaining organic solvents
  4. washThe adsorbed material is eluted with water-methanol (1:4)
  5. concentrationconcentrated
  6. customto give powder which
  7. washis washed with ethyl acetate

Sources & evidence

ORD record
ord-c62c4a49479841c5ae352a474ecf092c
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

Loading…