4-Nitrobenzoic Acid → HCID 66848190、化合物

HRID 536587

反応式

HRID 536587 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH2:21][OH:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:23]([C:26]1[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=1)([O-:25])=[O:24].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH2:21][O:22][C:30](=[O:31])[C:29]1[CH:28]=[CH:27][C:26]([N+:23]([O-:25])=[O:24])=[CH:34][CH:33]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 61084-Nitrobenzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 11078078tert-butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate2 回

生成物 1

HCID 66848190HCID 66848190、化合物

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

(2S,4R)-4-(Tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (intermediate 53, 51.4 g, 155 mmol) dissolved in 500 ml of dichloromethane was cooled to 0° C., then p-nitrobenzoic acid (28.5 g, 171 mmol), N,N′-dicyclohexylcarbodiimide (35.2 g, 171 mmol) and 4-dimethylaminopyridine (1.90 g, 1.60 mmol) were added. The mixture was maintained under stirring at room temperature for 18 hours, then filtrated; the filtrate was concentrated to obtain crude that was purified by silica gel chromatography (petroleum ether/ethyl acetate from 15/1 to 10/1). (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(4-nitro-benzoyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester was obtained as white solid (70 g, yield: 94%).

後処理

  1. temperatureThe mixture was maintained
  2. filtrationfiltrated
  3. concentrationthe filtrate was concentrated
  4. customto obtain crude that
  5. customwas purified by silica gel chromatography (petroleum ether/ethyl acetate from 15/1 to 10/1)

出典と根拠

ORDレコード
ord-aedafc3454554af78953524a7ae56442
出典データセット
uspto-grants-2014_10
特許番号
US08859608B2

関連ノート

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