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

HRID 540376ノート

反応式

HRID 540376 の反応式
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]

参加物

7

反応物 6

HCID 111,2-DichloroethaneHCID 6228Dimethylformamide2 回HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 669889253-Pentoxy-3-phenylazetidine trifluoroacetateHCID 87226379(R)-2-tert-butoxy-carbonylamino-3-(4-methoxyphenyl)propionic acid

生成物 1

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

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-7bbfae16ca6642b18548a117e1868995
出典データセット
uspto-grants-2014_10
特許番号
US08871187B2

反応ノート

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