Diisopropanolamine → 2-(3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-benzoylamino)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester

HRID 1094993

반응식

HRID 1094993 반응식
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[CH:6][C:5]=1[NH:16][C:17](=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24]Cl)[CH:19]=1.C(N(CC)CC)C.[CH3:35][CH:36]([OH:43])[CH2:37][NH:38][CH2:39][CH:40]([OH:42])[CH3:41].COC1C=C(C=CC=1OC)C(Cl)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[CH:6][C:5]=1[NH:16][C:17](=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][N:38]([CH2:39][CH:40]([OH:42])[CH3:41])[CH2:37][CH:36]([OH:43])[CH3:35])[CH:19]=1

참가 물질

6

반응물 4

HCID 8086DiisopropanolamineHCID 8471TriethylamineHCID 77070Veratroyl chlorideHCID 66638905HCID 66638905, 화합물

생성물 1

HCID 666387772-(3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-benzoylamino)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester수율 47%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Subsequently, 2-(3-chloromethyl-benzoylamino)-5-(2-oxo-pyrrolidin-1-yl)benzoic acid methyl ester (14 mg) was dissolved in anhydrous methylene chloride (5 ml). Triethylamine (7 mg: dissolved in 2 ml of anhydrous methylene chloride) and diisopropanolamine (compound B′) (10 mg: dissolved in 2 ml of anhydrous methylene chloride) were added dropwise to the solution at 0° C., and the mixture was stirred at room temperature for 24 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-{[bis-(2-hydroxy-propyl)-amino]-methyl}-benzoylamino)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (8.0 mg, yield 47%).

후처리

  1. additionwere added dropwise to the solution at 0° C.
  2. customAfter the completion of the reaction
  3. distillationdistilled water
  4. additionwas added
  5. extractionat room temperature, and the mixture was subjected to separatory extraction with chloroform
  6. washThe organic layer was washed with saturated brine
  7. dry with materialwas dried over sodium sulfate
  8. concentrationwas then concentrated under the reduced pressure
  9. customThe residue was purified by column chromatography
  10. washeluted with a chloroform-methanol system

출처 및 근거

ORD 기록
ord-a6b2a93b2dab46459bfeb6a8da32e9a3
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08134015B2

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