1,2-Dichloroethane → 3-(4-benzyloxyphenyl)-(R)-2-ethoxy-N-(2-hydroxy-(R)-1-phenylethyl)propanoic amide

HRID 1384422노트

반응식

HRID 1384422 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([O:20][CH2:21][CH3:22])[C:17]([OH:19])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.[CH:46]1[CH:51]=[CH:50][C:49]([CH:52]([NH2:55])[CH2:53][OH:54])=[CH:48][CH:47]=1>ClCCl.CCCCCCC.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C@@H:16]([O:20][CH2:21][CH3:22])[C:17]([NH:55][C@H:52]([C:49]2[CH:50]=[CH:51][CH:46]=[CH:47][CH:48]=2)[CH2:53][OH:54])=[O:19])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

9

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 924662-Amino-2-phenylethanolHCID 109245703-[4-(Benzyloxy)phenyl]-2-ethoxypropanoic acid

생성물 1

HCID 111226333-(4-benzyloxyphenyl)-(R)-2-ethoxy-N-(2-hydroxy-(R)-1-phenylethyl)propanoic amide수율 31%

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매HCID 8900Heptane용매

실험 절차

A solution of 3-(4-benzyloxyphenyl)-2-ethoxypropanoic acid (2.92 g, 9.74 mmole) in dry dichloromethane (30 ml) was cooled on an ice-bath and EDC (2.03g; 10.61 mmole), diisopropylethylamine (1.84 ml, 10.61 mmole) and HOBt x H2O (1.43 g; 10.61 mmole) were added. After 30 minutes the ice-bath was removed and (R)-phenylglycinol (1.46 g, 10.61 mmole) was added. After stirring at room temperature over night ethyl acetate (100 ml) was added and the mixture was washed with potassium hydrogensulfate (1 M), saturated sodium bicarbonate solution, sodium carbonate solution and brine. The organic phase was dried (sodium sulfate), filtered and the solvent was evaporated in vacuo. The crude product was purified by chromatography on silica gel using ethyl acetate:heptan to give 1.5 g (yield 37%) of 3-(4-benzyloxyphenyl)(S)-2-ethoxy-N-(2-hydroxy-(R)-1-phenylethyl)propanoic amide and 1.25 g (yield 31%) of 3-(4-benzyloxyphenyl)-(R)-2-ethoxy-N-(2-hydroxy-(R)-1-phenylethyl)propanoic amide.

후처리

  1. customAfter 30 minutes the ice-bath was removed
  2. additionwas added
  3. washthe mixture was washed with potassium hydrogensulfate (1 M), saturated sodium bicarbonate solution, sodium carbonate solution and brine
  4. dry with materialThe organic phase was dried (sodium sulfate)
  5. filtrationfiltered
  6. customthe solvent was evaporated in vacuo
  7. customThe crude product was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-56d94258a6754c22841d9f05e8d136d5
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06258850B1

반응 노트

불러오는 중…