Hydrochloric Acid → Efatutazone

HRID 412377Notes

Reaction equation

HRID 412377 reaction equation
C(OC([NH:8][C:9]1[C:49]([CH3:50])=[CH:48][C:12]([O:13][C:14]2[CH:15]=[CH:16][C:17]([NH:29][C:30](=O)[CH2:31][O:32][C:33]3[CH:38]=[CH:37][C:36]([CH2:39][CH:40]4[S:44][C:43](=[O:45])[NH:42][C:41]4=[O:46])=[CH:35][CH:34]=3)=[C:18]([N:20]([CH3:28])C(=O)OC(C)(C)C)[CH:19]=2)=[CH:11][C:10]=1[CH3:51])=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][C:9]1[C:49]([CH3:50])=[CH:48][C:12]([O:13][C:14]2[CH:15]=[CH:16][C:17]3[N:29]=[C:30]([CH2:31][O:32][C:33]4[CH:34]=[CH:35][C:36]([CH2:39][CH:40]5[S:44][C:43](=[O:45])[NH:42][C:41]5=[O:46])=[CH:37][CH:38]=4)[N:20]([CH3:28])[C:18]=3[CH:19]=2)=[CH:11][C:10]=1[CH3:51]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18537724t-butyl N-[5-(4-t-butoxycarbonylamino-3,5-dimethylphenoxy)-2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]phenyl]-N-methylcarbamate

Product 1

HCID 9832447EfatutazoneYield 19.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of t-butyl N-[5-(4-t-butoxycarbonylamino-3,5-dimethylphenoxy)-2-[4-(2,4dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]phenyl]-N-methylcarbamate (1.88 g) and 4N hydrogen chloride in 1,4-dioxane (20 ml) was stirred at room temperature for 23 hours. The reaction mixture was concentrated and water added to the residue. The mixture was neutralized with sodium bicarbonate and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on a silica gel column using ethyl acetate:n-hexane=2:1 as the eluant to afford the desired compound (0.26 g, mp 209-211° C.).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater added to the residue
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-258e9399a1fb4698a51d89d95e5cb032
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Reaction notes

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