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1-Hydroxybenzotriazole → 2-(4-Fluoro-phenylsulfanyl)-N-trityloxy-acetamide

HRID 1716318
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인쇄 미리보기

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HRID 1716318 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[C:13]([O:32][NH2:33])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O.O.CN1C(=O)CCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH2:9][C:10]([NH:33][O:32][C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:12])=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 7361972-[(4-Fluorophenyl)sulfanyl]acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3015602O-(triphenylmethyl)hydroxylamine

생성물 1

HCID 866199392-(4-Fluoro-phenylsulfanyl)-N-trityloxy-acetamide

시약·촉매·용매 4

HCID 962
Water
용매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매
HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

A mixture of (4-fluoro-phenylsulfanyl)-acetic acid (1.52 g, 8.17 mmol) from step B and O-Trityl-hydroxylamine (2.26 g, 10 mmol) in dry DMF was sequentially added NMP (3.0 ml), EDCl (2.05 g, 10.7 mmol), and HOBT (1.45 g, 10.74 mmol). The resulting mixture was stirred at room temperature for overnight. The reaction was diluted with EtOAc and water. The organic layer was washed sequentially with 1N HCl solution, 10% aqueous Na2CO3, water and saturated NaCl solution. The organic portion was dried over anhydrous Na2SO4 and concentrated under reduced pressure to gave a crude material, which was then purified by a column chromatography with 0˜25% EtOAc in hexanes. MS: 466.0 (M+H)+.

후처리

  1. washThe organic layer was washed sequentially with 1N HCl solution, 10% aqueous Na2CO3, water and saturated NaCl solution
  2. dry with materialThe organic portion was dried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-a60109d474054772818a90f4820ddbdc
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07803793B2

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