1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-3-{4-[1-(4-cyclohexylphenyl)-3-(3-methoxy-5-trifluoromethylphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid ethyl ester

HRID 967628노트

반응식

HRID 967628 반응식
C1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:13]([NH:23][C:24]([NH:26][C:27]2[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([O:37][CH3:38])[CH:28]=2)=[O:25])[C:14]2[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=2)CCCCC1.[CH:39]1[CH:40]=[CH:41][C:42]2N(O)N=N[C:43]=2[CH:44]=1.CCN=C=NCCCN(C)C.[CH2:60]([O:62][C:63](=[O:68])[C@H:64]([OH:67])[CH2:65][NH2:66])[CH3:61]>CN(C=O)C.C(OCC)(=O)C.O>[CH2:60]([O:62][C:63](=[O:68])[C@H:64]([OH:67])[CH2:65][NH:66][C:18](=[O:19])[C:17]1[CH:21]=[CH:22][C:14]([CH:13]([NH:23][C:24]([NH:26][C:27]2[CH:32]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:30]=[C:29]([O:37][CH3:38])[CH:28]=2)=[O:25])[C:8]2[CH:9]=[CH:10][C:11]([CH:39]3[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]3)=[CH:12][CH:7]=2)=[CH:15][CH:16]=1)[CH3:61]

참가 물질

8

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 223111384-[1-(Cyclohexylphenyl)-3-(3-methoxy-5-trifluoromethylphenyl)ureidomethyl]benzoic acidHCID 54263093ethyl (2R)-3-amino-2-hydroxypropanoate

생성물 1

HCID 67483036(R)-3-{4-[1-(4-cyclohexylphenyl)-3-(3-methoxy-5-trifluoromethylphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid ethyl ester수율 99.3%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

4-[1-(Cyclohexylphenyl)-3-(3-methoxy-5-trifluormethylphenyl)ureidomethyl]benzoic acid (420 mg, 0.8 mmol) was dissolved in DMF (10 mL), and then HOBt (160 mg, 1.2 mmol) and EDAC (230 mg, 1.2 mmol) were added. The reaction mixture was allowed to stand for 30 min, then (R)-isoserine ethyl ester (260 mg, 1.2 mmol) and dissopropylethylamine (210 mL, 1.2 mmol) dissolved in DMF (5 mL) were added and the reaction mixture was stirred at room temperature for 16 hours. Water (50 mL) and ethyl acetate (100 mL) were added and the organic phase was washed with water (5×50 mL), dried (magnesium sulphate), filtered and evaporated in vacuo. The residue was purified by column chromatography on silica gel, eluting with a mixture of heptane and ethyl acetate (1:3) to afford 510 mg of (R)-3-{4-[1-(4-cyclohexylphenyl)-3-(3-methoxy-5-trifluoromethylphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid ethyl ester as an amorphous solid.

후처리

  1. additionwere added
  2. washthe organic phase was washed with water (5×50 mL)
  3. dry with materialdried (magnesium sulphate)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with a mixture of heptane and ethyl acetate (1:3)

출처 및 근거

ORD 기록
ord-5828315428a943eb9238a822a9c4c7bf
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06953812B2

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