Triethylamine → N-[(1R,2Z)-2-amino-2-hydroxyimino-1-phenylethyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide

HRID 1964844Notes

Reaction equation

HRID 1964844 reaction equation
C(N(CC)CC)C.[C:8]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:13]=[CH:12][C:11]([S:14]([N:17]2[CH2:21][CH2:20][S:19][CH:18]2[C:22]([NH:24][CH:25]([C:32]#[N:33])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])(=[O:16])=[O:15])=[CH:10][CH:9]=1.Cl.[NH2:41][OH:42]>C(O)C>[NH2:33]/[C:32](=[N:41]\[OH:42])/[C@H:25]([NH:24][C:22]([CH:18]1[N:17]([S:14]([C:11]2[CH:12]=[CH:13][C:8]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[CH:9][CH:10]=2)(=[O:15])=[O:16])[CH2:21][CH2:20][S:19]1)=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 101739433-(biphenyl-4-ylsulfonyl)-N-[cyano(phenyl)methyl]-1,3-thiazolidine-2-carboxamide

Product 1

HCID 87519173N-[(1R,2Z)-2-amino-2-hydroxyimino-1-phenylethyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Triethylamine (92 μl, 0.66 mmol) was slowly added to a suspension of product Ic, e.g., 3-(biphenyl-4-ylsulfonyl)-N-[cyano(phenyl)methyl]-1,3-thiazolidine-2-carboxamide, and hydroxylamine.hydrochloride (46 mg, 0.66 mmol) in ethanol (5 mL), under stirring. The reaction mixture was heated under reflux for 16 h, and then cooled to RT. The solvents were removed and the resulting solid was suspended in water and extracted with three portions of EtOAc. Combined organic phases were dried over MgSO4, filtrated and evaporated, affording intermediate Id, e.g., N-[(1R,2Z)-2-amino-2-(hydroxyimino)-1-phenylethyl]-3-(biphenyl-4-ylsulfonyl)-1,3-thiazolidine-2-carboxamide (272 mg, quantitative yield) which was directly used in the next step.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 16 h
  3. customThe solvents were removed
  4. extractionextracted with three portions of EtOAc
  5. dry with materialCombined organic phases were dried over MgSO4
  6. filtrationfiltrated
  7. customevaporated

Sources & evidence

ORD record
ord-0a11f22ce438467681451891cc8fe01a
Source dataset
uspto-grants-2013_04
Patent number
US08415480B2

Reaction notes

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