Pyridine → (4-Nitrophenyl)methyl (2S,4S)-2-[[(aminosulfonyl)amino]methyl]-4-mercapto-1-pyrrolidinecarboxylate

HRID 1034483ノート

反応式

HRID 1034483 の反応式
[N+:1]([C:4]1[CH:44]=[CH:43][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:14][C@H:13]2[CH2:37][NH:38][S:39](=[O:42])(=[O:41])[NH2:40])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=CC=CC=1>O1CCCC1.O.ClCCl.CO.S.[N+]([O-])([O-])=O.[Ag+]>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([SH:17])[CH2:14][C@H:13]2[CH2:37][NH:38][S:39](=[O:41])(=[O:42])[NH2:40])=[O:11])=[CH:43][CH:44]=1)([O-:3])=[O:2]

参加物

9

反応物 2

HCID 1049PyridineHCID 57161027(2s,4s)-1-p-Nitrobenzyloxycarbonyl-2-sulfamoylaminomethyl-4-tritylthiopyrrolidine

生成物 1

HCID 10200398(4-Nitrophenyl)methyl (2S,4S)-2-[[(aminosulfonyl)amino]methyl]-4-mercapto-1-pyrrolidinecarboxylate収率 63%

試薬・触媒・溶媒 6

HCID 24470Silver Nitrate触媒HCID 402Hydrogen Sulfide溶媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-sulfamoylaminomethyl-4-tritylthiopyrrolidine (668 mg: 0.95 mmole) in tetrahydrofuran (6 ml), a solution of pyridine (0.254 ml: 2.7 eq.) and silver nitrate (403 mg: 2.5 eq.) in water (2 ml) is added under ice cooling. The mixture is stirred at room temperature for 1 hour. The reaction mixture is diluted with dichloromethane (3 ml) and methanol (3 ml), and hydrogen sulfide is bubbled through it under ice cooling for 10 minutes. The resulting precipitate is removed by filtering. The filtrate is diluted with dichloromethane, washed with water, dried over magnesium sulfate, and concentrated in vacuo. The residue is purified by silica gel column chromatography (toluene: ethyl acetate) to give (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-sulfamoylaminomethyl-4-mercaptopyrrolidine (233 mg). Yield: 63%. NMR δ(CDCl3 -CD3OD) ppm: 1.42(t, J=7 Hz, 1H), 1.65 to 1.93(m, 1H), 2.48 to 2.70 (m, 1H), 3.05 to 3.63(m, 4H), 3.93 to 4.16(m, 2H), 5.22(s, 2H), 7.53(d, J=8 Hz, 2H), 8.23(d, J=8 Hz, 2H). IR ν (CHCl3) cm-1 : 3276br, 1692, 1607.

後処理

  1. customis bubbled through it under ice cooling for 10 minutes
  2. customThe resulting precipitate is removed
  3. filtrationby filtering
  4. additionThe filtrate is diluted with dichloromethane
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel column chromatography (toluene: ethyl acetate)

出典と根拠

ORDレコード
ord-0207ada31fd342cf86e23cafffcbd290
出典データセット
uspto-grants-1994_05
特許番号
US05317016

反応ノート

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