Aluminum(III) Chloride → HCID 178481178, compound

HRID 1707484Notes

Reaction equation

HRID 1707484 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[CH2:64][S:65][C:66]2[N:67]=[N:68][N:69]([CH3:71])[CH:70]=2)=[S:16])C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-]>C1(OC)C=CC=CC=1.[N+](C)([O-])=O.Cl.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:14])=[S:16])=[C:18]([CH2:64][S:65][C:66]4[N:67]=[N:68][N:69]([CH3:71])[CH:70]=4)[CH2:19][S:20][C@H:21]23)=[O:62])[N:50]=1

Participants

7

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 141566156O-benzhydryl (6R,7R)-7-[[(2Z)-2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-trityloxyiminoacetyl]amino]-3-[(1-methyltriazol-4-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbothioate

Product 1

HCID 178481178HCID 178481178, compoundYield 27.5%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6375NitromethaneSolventHCID 7519AnisoleSolvent2×

Procedure

To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-(1-methyl-1,2,3-triazol-4-yl)thiomethylthio-3-cephem-4-carboxylic acid diphenylmethyl ester (708 mg: 0.683 mMol.) in a mixture of anisole (2 ml) and nitromethane (8 ml) is added dropwise a solution of aluminum chloride (727 mg: 5.47 mMol.) in anisole (2 ml) at -40° C., and the mixture is stirred for 1 hour at -30°--40° C. The reaction mixture is diluted with 1N-hydrochloric acid (5.5 ml) and water and washed with ethyl acetate. The aqueous layer is concentrated under reduced pressure to remove organic solvent and passed through a column of styrene-divinylbenzene copolymer adsorbent. The product is eluted with methanol-water (4:1) to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-(1-methyl-1,2,3-triazol-4-yl)thiomethylthio-3-cephem-4carboxylic acid as pale yellow powder (96.3 mg). Yield: 27%.

Workup

  1. washwashed with ethyl acetate
  2. concentrationThe aqueous layer is concentrated under reduced pressure
  3. customto remove organic solvent
  4. washThe product is eluted with methanol-water (4:1)

Sources & evidence

ORD record
ord-bc73af517f7c449a9c503fdef8af04d5
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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