Chloroform → (1S)-3-(3-chlorophenyl)-3-cyano-1-(2-[(phenylmethyl)oxy]ethyl}propyl 4-methylbenzenesulfonate

HRID 2099294ノート

反応式

HRID 2099294 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([CH2:11][C@H:12]([OH:23])[CH2:13][CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.[C:24]1(C)[C:25]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:27]=[CH:28][CH:29]=1.[CH:35](Cl)(Cl)Cl>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:35][C:28]1[CH:29]=[CH:24][C:25]([S:30]([O:23][C@H:12]([CH2:13][CH2:14][O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:11][CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[C:9]#[N:10])(=[O:31])=[O:32])=[CH:26][CH:27]=1

参加物

6

反応物 3

HCID 6212ChloroformHCID 8623o-Toluenesulfonyl chlorideHCID 57794819(4S)-2-(3-chlorophenyl)-4-hydroxy-6-[(phenylmethyl)oxy]hexanenitrile

生成物 1

HCID 57794796(1S)-3-(3-chlorophenyl)-3-cyano-1-(2-[(phenylmethyl)oxy]ethyl}propyl 4-methylbenzenesulfonate収率 66%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

実験手順

To a solution of (4S)-2-(3-chlorophenyl)-4-hydroxy-6-[(phenylmethyl)oxy]hexanenitrile (6.00 g, 18.2 mmol) in 50% CHCl3 in pyridine at 0° C. was added DMAP (2.22 g) and toluenesulfonyl chloride (10.4 g, 54.5 mmol). After warming to room temperature over several hours, the reaction mixture was stored in the freezer for 2 days. After an aqueous work up with 1N HCl the organic layer was dried over MgSO4 and evaporated to an oil. Chromatography on silica with 25% EtOAc in Hexanes afforded the title compound (5.68 g, 66%) as a yellow oil. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.9 (m, 2H) 2.1 (m, 2H) 2.3 (m, 2H) 2.4 (s, 3H) 3.4 (m, 1H) 3.5 (m, 1H) 4.4 (m, 2H) 7.1 (m, 1H) 7.3 (m, 10H) 7.8 (m, 2H)

後処理

  1. dry with materialAfter an aqueous work up with 1N HCl the organic layer was dried over MgSO4
  2. customevaporated to an oil

出典と根拠

ORDレコード
ord-dd73e190a45840f6a9b124589ed866b1
出典データセット
uspto-grants-2009_08
特許番号
US07569579B2

反応ノート

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