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Pyridine → 3-benzyloxy-4-[(S)-2-tert-butoxycarbonyl-1-(methoxy-methyl-carbamoyl)-ethylsulfamoyl]-benzoic acid methyl ester

HRID 1814329
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HRID 1814329 반응식
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[C:6]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:5]=1.[C:23]([O:27][C:28](=[O:38])[CH2:29][C@H:30]([NH2:37])[C:31]([N:33]([O:35][CH3:36])[CH3:34])=[O:32])([CH3:26])([CH3:25])[CH3:24].N1C=CC=CC=1>ClCCl.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([S:10](=[O:12])(=[O:11])[NH:37][C@H:30]([C:31](=[O:32])[N:33]([O:35][CH3:36])[CH3:34])[CH2:29][C:28]([O:27][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:38])=[C:6]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:5]=1
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참가 물질

6

반응물 3

HCID 1049PyridineHCID 15895197(S)-3-amino-N-methoxy-N-methyl-succinamic acid tert-butyl esterHCID 865882243-Benzyloxy-4-chlorosulfonyl-benzoic acid methyl ester

생성물 1

HCID 865882233-benzyloxy-4-[(S)-2-tert-butoxycarbonyl-1-(methoxy-methyl-carbamoyl)-ethylsulfamoyl]-benzoic acid methyl ester수율 56.4%

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 3-benzyloxy-4-chlorosulfonyl-benzoic acid methyl ester (9.25 g, 27.1 mmol) in dichloromethane (270 mL) was added (S)-3-amino-N-methoxy-N-methyl-succinamic acid tert-butyl ester (6.30 g, 27.1 mmol) followed by pyridine (6.59 mL, 81.4 mmol). The reaction was allowed to stir over night at room temperature. The reaction was then diluted with ethyl acetate (500 mL) and washed sequentially with 5% citric acid, saturated sodium bicarbonate, and saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield an orange oil. The crude residue was chromatographed (silica gel, 40% ethyl acetate-60% hexane) to give 3-benzyloxy-4-[(S)-2-tert-butoxycarbonyl-1-(methoxy-methyl-carbamoyl)-ethylsulfamoyl]-benzoic acid methyl ester as a white foam (8.20 g, 56%). 1H NMR(300 MHz, DMSO) 7.84 (d, 1H), 7.60 (m, 1H), 7.57 (m, 2H), 7.52 (d, 2H), 7.36 (t, 2H), 7.28 (t, 1H), 5.35 (s, 2H), 4.60 (m, 1H), 3.81 (s, 3H), 3.48 (bs, 3H), 2.82 (bs, 3H), 2.46 (dd, 1H), 2.33 (dd, 1H), 1.27 (s, 9H). MS(APCI) m/z 535.2 (M−H).

후처리

  1. washwashed sequentially with 5% citric acid, saturated sodium bicarbonate, and saturated sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto yield an orange oil
  6. customThe crude residue was chromatographed (silica gel, 40% ethyl acetate-60% hexane)

출처 및 근거

ORD 기록
ord-ba744378360e4dc6b33025a5eb268dc6
출처 데이터셋
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06875765B2

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