2-(Methylthio)thiazole → HCID 178474897, compound

HRID 2164984Notes

Reaction equation

HRID 2164984 reaction equation
[CH2:1]([O:3]/[N:4]=[C:5](/[C:36]1[N:37]=[C:38]([NH:41]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:39][CH:40]=1)\[C:6]([NH:8][CH:9]1[C:34](=[O:35])[N:11]2[C:12]([C:18]([O:20]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:19])=[C:13]([CH2:16]I)[CH2:14][S:15][C@H:10]12)=[O:7])[CH3:2].[CH3:61][S:62][C:63]1[S:64][CH:65]=[CH:66][N:67]=1>C(Cl)Cl.C(Cl)(Cl)Cl.[B-](F)(F)(F)F.[Ag+]>[NH2:41][C:38]1[S:39][CH:40]=[C:36](/[C:5](=[N:4]/[O:3][CH2:1][CH3:2])/[C:6]([NH:8][CH:9]2[C:34](=[O:35])[N:11]3[C:12]([C:18]([O-:20])=[O:19])=[C:13]([CH2:16][N+:67]4[CH:66]=[CH:65][S:64][C:63]=4[S:62][CH3:61])[CH2:14][S:15][C@H:10]23)=[O:7])[N:37]=1

Participants

6

Reactant 2

HCID 27601002-(Methylthio)thiazoleHCID 88600798benzhydryl (6R)-7-[[(2Z)-2-ethoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-3-(iodomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Product 1

HCID 178474897HCID 178474897, compoundYield 145.6%

Reagents, catalysts & solvents 3

HCID 159722Silver tetrafluoroborateCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of diphenylmethyl 7-[(Z)-2-(ethoxyimino)-2-(2-tritylaminothiazol-4-yl)acetamido]-3-iodomethyl-3-cephem-4-carboxylate [VII-2] (517 mg, 0.55 mmole) and 2-methylthiothiazole (85.3 mg, 0.65 mmole) in CH2Cl2 (10 ml) was added AgBF4 (117 mg, 0.60 mmole) and the mixture was stirred for 1.5 hours at room temperature. The reaction mixture was diluted with CHCl3 (100 mL), and the resulting precipitate was recovered by filtration and washed with CHCl3 (100 mL). The filtrate and the washings were combined and washed with water, dried over MgSO4 and evaporated. The residue was triturated with ether (50 mL) to give an amorphous solid (433 mg), which was dissolved in 90% TFA. The mixture was allowed to stand for 45 minutes at room temperature and then evaporated in vacuo at 10° C. The residue was triturated with ether to give crude Id (291 mg) which was dissolved in a small amount of methanol and passed through an HP-20 (20 mL) column by eluting with 30% aqueous methanol, to give 63.3 mg (29%) of the title compound [Id]. Estimated purity 70%.

Workup

  1. filtrationthe resulting precipitate was recovered by filtration
  2. washwashed with CHCl3 (100 mL)
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was triturated with ether (50 mL)

Sources & evidence

ORD record
ord-ce141a6285b94119995dcc3b02021cee
Source dataset
uspto-grants-1985_03
Patent number
US04507487

Reaction notes

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