Dimethylformamide → 3-{4-[1-(4-Tert-butylphenyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid ethyl ester

HRID 967641ノート

反応式

HRID 967641 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:27]2[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=2C(O)=O)[NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=2)=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].ON1C2N=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl.[CH2:58]([O:60][C:61](=[O:66])[CH:62]([OH:65])[CH2:63][NH2:64])[CH3:59].C(N(C(C)C)CC)(C)C.CN([CH:79]=[O:80])C>C(Cl)Cl>[CH2:58]([O:60][C:61](=[O:66])[CH:62]([OH:65])[CH2:63][NH:64][C:79](=[O:80])[C:33]1[CH:32]=[CH:28][C:27]([CH:11]([NH:12][C:13]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][C:23]([F:25])([F:26])[F:24])=[CH:20][CH:21]=2)=[O:14])[C:8]2[CH:9]=[CH:10][C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])=[CH:6][CH:7]=2)=[CH:35][CH:34]=1)[CH3:59]

参加物

8

反応物 6

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 22311167[1-(4-Tert-butylphenyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]benzoic acidHCID 85611992(RS)-isoserine ethyl ester hydrochloride

生成物 1

HCID 674831433-{4-[1-(4-Tert-butylphenyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid ethyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of [1-(4-tert-butylphenyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]benzoic acid (1.0 g, 2.06 mmol) in DMF (1 mL) and DCM (10 mL) was added 1-hydroxy-7-azabenzotriazole (0.33 g, 2.47 mmol). After stirring for 1 hour at room temperature, EDAC (0.47 g, 2.47 mmol), (RS)-isoserine ethyl ester hydrochloride (0.52 g, 3.09 mmol) and diisopropylethylamine (1.1 mL, 6.18 mmol) were added, successively. After stirring for 17 hours at ambient temperature the reaction mixture was partitioned between water, brine and ethyl acetate. The aqueous phase was further extracted with ethyl acetate. The combined organic phases were washed with water and brine. After drying (magnesium sulphate) and filtration, the organic phase was evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (6:4). This afforded 1.2 g (97%) of (RS)-3-{4-[1-(4-tert-butylphenyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid ethyl ester as an oil.

後処理

  1. stirringAfter stirring for 17 hours at ambient temperature the reaction mixture
  2. customwas partitioned between water, brine and ethyl acetate
  3. extractionThe aqueous phase was further extracted with ethyl acetate
  4. washThe combined organic phases were washed with water and brine
  5. customAfter drying
  6. filtration(magnesium sulphate) and filtration
  7. customthe organic phase was evaporated in vacuo
  8. customThe residue was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (6:4)

出典と根拠

ORDレコード
ord-a82ed14995db4b599edba2a8e9e30f9c
出典データセット
uspto-grants-2005_10
特許番号
US06953812B2

反応ノート

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