1,2-Dichloroethane → tert-butyl[(R)-1-(4-methoxy-benzyl)-2-oxo-2-(3-pentyloxy-3-o-tolylazetidin-1-yl)ethyl]carbamate

HRID 540376노트

반응식

HRID 540376 반응식
C(O[C@:6]([N:19]=[C:20]=[O:21])([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[C:7]([OH:9])=O)(C)(C)C.[CH2:22](Cl)[CH2:23]Cl.[CH:26]1[CH:27]=[CH:28][C:29]2N(O)N=N[C:30]=2[CH:31]=1.F[C:37](F)(F)[C:38]([OH:40])=O.C([O:48][C:49]1([C:53]2C=CC=CC=2)[CH2:52]N[CH2:50]1)CCCC.CCN([CH:65]([CH3:67])[CH3:66])C(C)C.C[N:69]([CH:71]=O)[CH3:70]>>[C:49]([O:48][C:20](=[O:21])[NH:19][C@H:6]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1)[C:7](=[O:9])[N:69]1[CH2:70][C:38]([O:40][CH2:67][CH2:65][CH2:66][CH2:22][CH3:23])([C:37]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:26])[CH2:71]1)([CH3:53])([CH3:52])[CH3:50]

참가 물질

7

반응물 6

HCID 111,2-DichloroethaneHCID 6228Dimethylformamide2회HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 669889253-Pentoxy-3-phenylazetidine trifluoroacetateHCID 87226379(R)-2-tert-butoxy-carbonylamino-3-(4-methoxyphenyl)propionic acid

생성물 1

HCID 131731973tert-butyl[(R)-1-(4-methoxy-benzyl)-2-oxo-2-(3-pentyloxy-3-o-tolylazetidin-1-yl)ethyl]carbamate수율 56%

실험 절차

2.93 g (9.93 mmol) of (R)-2-tert-butoxy-carbonylamino-3-(4-methoxyphenyl)propionic acid are dissolved in 10 ml of DMF. 2.08 g (10.9 mmol) of EDC, 1.47 g (10.9 mmol) of HOBt and a solution of 3.45 g (9.93 mmol) of 3-pentoxy-3-phenylazetidine trifluoro-acetate in 15 ml of DMF are then added. 7 ml (40.2 mmol) of DIEA are added. The reaction medium is stirred at ambient temperature for 2 h 30 and then extracted with ethyl acetate. The organic phase is washed with 1N sodium hydroxide and then dried over magnesium sulphate, filtered and evaporated. The crude product obtained is purified by silica gel chromatography (eluent 6/4 heptane/ethyl acetate). 2.83 g in the form of a white powder are obtained with a yield of 56%.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with 1N sodium hydroxide
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated

출처 및 근거

ORD 기록
ord-7bbfae16ca6642b18548a117e1868995
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871187B2

반응 노트

불러오는 중…