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

HRID 1964844ノート

反応式

HRID 1964844 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0a11f22ce438467681451891cc8fe01a
出典データセット
uspto-grants-2013_04
特許番号
US08415480B2

反応ノート

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