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Tetrahydrofuran → Ethyl (4-{[2-(3-benzyl-ureido)-thiazole-4-carbonyl]-amino}-phenoxy)-acetate

HRID 378997
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반응식

HRID 378997 반응식
[CH2:1]([NH:8][C:9](=[O:19])[NH:10][C:11]1[S:12][CH:13]=[C:14]([C:16]([OH:18])=O)[N:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.Cl.[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:29][CH:28]=1>C(OCC)(=O)C>[CH2:1]([NH:8][C:9](=[O:19])[NH:10][C:11]1[S:12][CH:13]=[C:14]([C:16]([NH:26][C:27]2[CH:28]=[CH:29][C:30]([O:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:31][CH:32]=2)=[O:18])[N:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 183228652-(3-Benzyl-ureido)-thiazole-4-carboxylic acidHCID 21697723Ethyl 4-amino-phenyloxyacetate hydrochloride

생성물 1

HCID 54538745Ethyl (4-{[2-(3-benzyl-ureido)-thiazole-4-carbonyl]-amino}-phenoxy)-acetate수율 51%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

419 mg of 2-(3-benzyl-ureido)-thiazole-4-carboxylic acid, 265 mg of CDMT, 4.5 ml of THF and 0.18 ml of N-MM are 4.5 hrs. at RT. After the addition of 350 mg of ethyl 4-amino-phenyloxyacetate hydrochloride and 0.18 ml of N-MM the mixture is stirred for a further 20 hrs. at RT. For the working up, the mixture is diluted with ethyl acetate and washed in succession with dilute hydrochloric acid, water, dilute sodium carbonate solution, water and saturated sodium chloride solution, dried over sodium sulphate and evaporated in a vacuum. Chromatography on silica gel with methylene chloride-alcohol 99:1 and crystallization from ether gives 350 mg of ethyl (4-{[2-(3-benzyl-ureido)-thiazole-4-carbonyl]-amino}-phenoxy)-acetate, m.p. 173° C., MS: 455 (M+H)+.

후처리

  1. customat RT
  2. customat RT
  3. washwashed in succession with dilute hydrochloric acid, water, dilute sodium carbonate solution, water and saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated in a vacuum
  6. customChromatography on silica gel with methylene chloride-alcohol 99:1 and crystallization from ether

출처 및 근거

ORD 기록
ord-cb26e731ec744ddc98e4a3fbb5cf9fae
출처 데이터셋
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06297266B1

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