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

HRID 1814329
ノート
印刷プレビュー

反応式

HRID 1814329 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344
Dichloromethane
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-ba744378360e4dc6b33025a5eb268dc6
出典データセット
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06875765B2

反応ノート

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