Triethylamine → N-(tert-butoxy)-2-[1-(4-phenoxyphenylthio)cyclopent-1-yl]-acetamide

HRID 1584395ノート

反応式

HRID 1584395 の反応式
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14][C:15]2([CH2:20][C:21]([OH:23])=O)[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:25]([O:29][NH2:30])([CH3:28])([CH3:27])[CH3:26].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:25]([O:29][NH:30][C:21](=[O:23])[CH2:20][C:15]1([S:14][C:11]2[CH:12]=[CH:13][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:9][CH:10]=2)[CH2:16][CH2:17][CH2:18][CH2:19]1)([CH3:28])([CH3:27])[CH3:26]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 212241652-[1-(4-Phenoxyphenylthio)-cyclopent-1-yl]-acetic acid

生成物 1

HCID 21224113N-(tert-butoxy)-2-[1-(4-phenoxyphenylthio)cyclopent-1-yl]-acetamide

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

実験手順

The 2-[1-(4-phenoxyphenylthio)-cyclopent-1-yl]-acetic acid obtained in Example 5 was dissolved in methylene chloride (8 ml) and treated with 4 -dimethylaminopyridine (180 mg), O-(tert-butyl) hydroxylamine hydrochloride (360 mg), triethylamine (540 μL), pyridine (400 μL), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (750 mg). After stirring overnight the reaction mixture was partitioned between ethyl acetate and water, the organic layer separated, and the solvent removed under reduced pressure. Preparative TLC of the residue and elution with 2:1 hexane/ethyl acetate gave N-(tert-butoxy)-2-[1-(4-phenoxyphenylthio)cyclopent-1-yl]-acetamide (270 mg) as a white foam, which can be used in the next reaction without further purification.

後処理

  1. customwas partitioned between ethyl acetate and water
  2. customthe organic layer separated
  3. customthe solvent removed under reduced pressure
  4. washPreparative TLC of the residue and elution with 2:1 hexane/ethyl acetate

出典と根拠

ORDレコード
ord-90e8552d1e1b40fdaff4e76175dbaefe
出典データセット
uspto-grants-1999_08
特許番号
US05932595

反応ノート

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