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

HRID 2099294노트

반응식

HRID 2099294 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

실험 절차

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)

후처리

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

출처 및 근거

ORD 기록
ord-dd73e190a45840f6a9b124589ed866b1
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569579B2

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