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Benzoic acid, 4-amino-, 1,1-dimethylethyl ester → benzyl (2S,4S)-2-[(4-{[(2-methyl-2-propanyl)oxy]carbonyl}phenyl)carbamoyl]-4-[4-(methylsulfonyl)-1-piperazinyl]-1-pyrrolidinecarboxylate

HRID 1053812
ノート
印刷プレビュー

反応式

HRID 1053812 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@H:14]([N:16]2[CH2:21][CH2:20][N:19]([S:22]([CH3:25])(=[O:24])=[O:23])[CH2:18][CH2:17]2)[CH2:13][C@H:12]1[C:26](O)=[O:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:29][C:30]1[CH:42]=[CH:41][C:33]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[CH:32][CH:31]=1>N1C=CC=CC=1>[CH3:40][C:37]([O:36][C:34]([C:33]1[CH:41]=[CH:42][C:30]([NH:29][C:26]([C@@H:12]2[CH2:13][C@H:14]([N:16]3[CH2:21][CH2:20][N:19]([S:22]([CH3:25])(=[O:24])=[O:23])[CH2:18][CH2:17]3)[CH2:15][N:11]2[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])=[O:27])=[CH:31][CH:32]=1)=[O:35])([CH3:38])[CH3:39]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 118107654(2S,4S)-1-[(benzyloxy)carbonyl]-4-[4-(methylsulfonyl)-1-piperazinyl]-2-pyrrolidinecarboxylic acid

生成物 1

HCID 122584929benzyl (2S,4S)-2-[(4-{[(2-methyl-2-propanyl)oxy]carbonyl}phenyl)carbamoyl]-4-[4-(methylsulfonyl)-1-piperazinyl]-1-pyrrolidinecarboxylate収率 78.8%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a solution of the compound prepared in Example 4 (0.20 g, 0.40 mmol) and 2-methyl-2-propanyl 4-aminobenzoate (0.154 g, 0.80 mmol) in pyridine (50 mL) was added 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (0.630 mg 3.2 mmol) at 0° C. The reaction was stirred at room temperature for 18 h. The mixture was concentrated under reduced pressure and the resulting residue diluted with dichloromethane (20 mL). This solution was washed with brine, dried and concentrated. Purification by flash chromatography (silica gel, 40 g, 20-80% ethyl acetate/hexanes) gave the title compound (0.185 g, 65%) as a white solid.

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe resulting residue diluted with dichloromethane (20 mL)
  3. washThis solution was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customPurification by flash chromatography (silica gel, 40 g, 20-80% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-cfd8b255b343423ebabc91563bc2287d
出典データセット
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09394250B2

反応ノート

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