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

HRID 1584395노트

반응식

HRID 1584395 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-90e8552d1e1b40fdaff4e76175dbaefe
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05932595

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