Nitromethane → HCID 178481917, compound

HRID 1707485Notes

Reaction equation

HRID 1707485 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[CH:70]=[N:69][N:68]([CH3:71])[N:67]=2)=[S:16])C2C=CC=CC=2)C=CC=CC=1.[N+](C)([O-])=O.[Cl-].[Al+3].[Cl-].[Cl-]>C1(OC)C=CC=CC=1.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[CH:70]=[N:69][N:68]([CH3:71])[N:67]=4)[CH2:19][S:20][C@H:21]23)=[O:62])[N:50]=1

Participants

7

Reactant 3

HCID 6375NitromethaneHCID 6451240Aluminum(III) ChlorideHCID 141566124HCID 141566124, compound

Product 1

HCID 178481917HCID 178481917, compoundYield 77.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 7519AnisoleSolvent2×

Procedure

To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-(2-methyl-1,2,3-triazol-4-yl)thiomethylthio-3-cephem-4-carboxylic acid diphenylmethyl ester (1.39 g: 1.34 mMol.) in a mixture anisole (5 ml) and nitromethane (20 ml) is added dropwise a solution of aluminum chloride (1.43 g: 10.8 mMol.) in anisole (5 ml) at -40° C. After stirring at -30° to -40° C. for 1 hour, the mixture is diluted with 1N-hydrochloric acid (11 ml) and water and washed with ethyl acetate. The aqueous layer is concentrated under reduced pressure to remove organic solvents 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-(2-methyl-1,2,3-triazol-4-yl)thiomethylthio-3-cephem-4-carboxylic acid as pale yellow powder (534 mg). Yield: 75%.

Workup

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

Sources & evidence

ORD record
ord-8c3550313d064a62a45c953f93bb0629
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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