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Pyridine → 3-Benzyloxy-4-((S)-2-tert-butoxycarbonyl-1-carbamoyl-ethylsulfamoyl)-benzoic acid methyl ester

HRID 1814377
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반응식

HRID 1814377 반응식
C(Cl)Cl.[CH3:4][O:5][C:6](=[O:25])[C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[C:9]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:8]=1.[C:26]([O:30][C:31](=[O:38])[CH2:32][C@H:33]([NH2:37])[C:34]([NH2:36])=[O:35])([CH3:29])([CH3:28])[CH3:27].N1C=CC=CC=1>C(OCC)(=O)C>[CH3:4][O:5][C:6](=[O:25])[C:7]1[CH:12]=[CH:11][C:10]([S:13](=[O:15])(=[O:14])[NH:37][C@H:33]([C:34](=[O:35])[NH2:36])[CH2:32][C:31]([O:30][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:38])=[C:9]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:8]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 7019655L-Aspartic alpha-amide beta-t-butyl esterHCID 865882243-Benzyloxy-4-chlorosulfonyl-benzoic acid methyl ester

생성물 1

HCID 697302973-Benzyloxy-4-((S)-2-tert-butoxycarbonyl-1-carbamoyl-ethylsulfamoyl)-benzoic acid methyl ester수율 45%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a room temperature CH2Cl2 solution (400 mL) of 3-benzyloxy-4-chlorosulfonyl-benzoic acid methyl ester (11.43 g, 33.50 mmol) was added (S)-3-amino-succinamic acid tert-butyl ester (6.32 g, 33.50 mmol) and pyridine (10.80 mL). The reaction mixture was allowed to stir for 12 h at room temperature. The reaction was then diluted with ethyl acetate and washed with 5% citric acid and saturated NaHCO3. The organic phase was dried (MgSO4), and then the solvent was removed under vacuum. The resulting crude product was purified using silica gel flash chromatography (3% MeOH in CH2Cl2). 3-Benzyloxy-4-((S)-2-tert-butoxycarbonyl-1-carbamoyl-ethylsulfamoyl)-benzoic acid methyl ester was obtained in 45% yield (7.40 g) as an off white foam. MS m/z 491.2 (M−1).

후처리

  1. washwashed with 5% citric acid and saturated NaHCO3
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customthe solvent was removed under vacuum
  4. customThe resulting crude product was purified

출처 및 근거

ORD 기록
ord-725dfbf350364d38a96f5a25d43022d9
출처 데이터셋
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06875765B2

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