Methanesulfonic Acid → HCID 13960529, compound

HRID 2413443Notes

Reaction equation

HRID 2413443 reaction equation
CS(O)(=O)=O.[CH:6]([O:19][C:20]([C:22]1[N:23]2[CH:26]([S:27][CH2:28][C:29]=1[C:30]1[S:34][C:33]([CH2:35][C:36]3[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=3)=[N:32][CH:31]=1)[CH:25]([NH:42]C(OC(C)(C)C)=O)[C:24]2=[O:50])=[O:21])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(#N)C>[NH2:42][CH:25]1[C:24](=[O:50])[N:23]2[CH:26]1[S:27][CH2:28][C:29]([C:30]1[S:34][C:33]([CH2:35][C:36]3[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=3)=[N:32][CH:31]=1)=[C:22]2[C:20]([O:19][CH:6]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:21]

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 20402446HCID 20402446, compound

Product 1

HCID 13960529HCID 13960529, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of methanesulphonic acid (10 cc) is added to a solution of 2-benzhydroxycarbonyl-7-t-butoxycarbonylamino-8-oxo-3-[2-(pyrid-3-ylmethyl)-thiazol-5-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene (10 g) in acetonitrile (100 cc). The mixture is stirred for 5 minutes and is poured into a 50:50 (by volume) mixture (500 cc) of saturated sodium bicarbonate solution and ethyl acetate. The organic phase is decanted and then washed successively with distilled water (200 cc) and saturated sodium chloride solution (200 cc). It is dried over anhydrous magnesium sulphate and filtered, and the filtrate is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C. 7-Amino-2-benzhydryloxycarbonyl-8-oxo-3-[2-(pyrid-3-yl-methyl)-thiazol-5-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene (6.36 g) is obtained in the form of a chestnut-coloured froth.

Workup

  1. customThe organic phase is decanted
  2. washwashed successively with distilled water (200 cc) and saturated sodium chloride solution (200 cc)
  3. dry with materialIt is dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C

Sources & evidence

ORD record
ord-1d5216dba70a4236bc4090cfb084cfbc
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

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