p-Toluenesulfonic acid → HCID 86585316, compound

HRID 1358887Notes

Reaction equation

HRID 1358887 reaction equation
O.[NH2:2][NH2:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH:15][C:16]1[CH:33]=[CH:32][C:31]2[C@@H:30]3[C@H:21]([C@H:22]4[C@@:26]([CH2:28][C@@H:29]3[C:34]3[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][S:46]([CH2:49][CH2:50][CH2:51][C:52]([F:58])([F:57])[C:53]([F:56])([F:55])[F:54])(=[O:48])=[O:47])=[CH:36][CH:35]=3)([CH3:27])[C:25](=O)[CH2:24][CH2:23]4)[CH2:20][CH2:19][C:18]=2[CH:17]=1.C(=O)(O)[O-].[Na+]>CO>[OH:15][C:16]1[CH:33]=[CH:32][C:31]2[C@@H:30]3[C@H:21]([C@H:22]4[C@@:26]([CH2:28][C@@H:29]3[C:34]3[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][S:46]([CH2:49][CH2:50][CH2:51][C:52]([F:58])([F:57])[C:53]([F:56])([F:55])[F:54])(=[O:48])=[O:47])=[CH:36][CH:35]=3)([CH3:27])[C:25](=[N:2][NH2:3])[CH2:24][CH2:23]4)[CH2:20][CH2:19][C:18]=2[CH:17]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 21138145HCID 21138145, compound

Product 1

HCID 86585316HCID 86585316, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

100 μl of hydrazine hydrate and 3 mg of paratoluenesulphonic acid are added to 300 mg of the product obtained in Example 73 in 3 cm3 of methanol. Agitation is carried out for 16 hours at ambient temperature, 50 cm3 of an aqueous solution of sodium bicarbonate is added, extraction is carried out with methylene chloride, the solvent is evaporated off, the residue is chromatographed on silica (eluant: ethyl acetate) and 190 mg of expected product is obtained.

Workup

  1. extractionextraction
  2. customthe solvent is evaporated off
  3. customthe residue is chromatographed on silica (eluant: ethyl acetate)

Sources & evidence

ORD record
ord-125ce721168b450db5c9db713616850b
Source dataset
uspto-grants-2003_07
Patent number
US06596885B2

Reaction notes

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