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

HRID 279683노트

반응식

HRID 279683 반응식
C(Cl)CCl.C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.O.[CH2:25]([O:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH:40]([O:44][CH2:45][CH3:46])[C:41]([OH:43])=[O:42])=[CH:35][CH:34]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[CH:47]1[CH:52]=[CH:51][C:50]([CH:53]([NH2:56])[CH2:54][OH:55])=[CH:49][CH:48]=1>ClCCl.CCCCCCC.C(OCC)(=O)C>[CH2:25]([O:32][C:33]1[CH:34]=[CH:35][C:36]([CH2:39][C@H:40]([O:44][CH2:45][CH3:46])[C:41]([NH:56][C@H:53]([C:50]2[CH:51]=[CH:52][CH:47]=[CH:48][CH:49]=2)[CH2:54][OH:55])=[O:43])=[CH:37][CH:38]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1.[CH2:25]([O:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][C@@H:40]([O:44][CH2:45][CH3:46])[C:41]([NH:56][C@H:53]([C:50]2[CH:51]=[CH:52][CH:47]=[CH:48][CH:49]=2)[CH2:54][OH:55])=[O:42])=[CH:35][CH:34]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

참가 물질

11

반응물 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 924662-Amino-2-phenylethanolHCID 109245703-[4-(Benzyloxy)phenyl]-2-ethoxypropanoic acid

생성물 2

HCID 111226333-(4-benzyloxyphenyl)-(R)-2-ethoxy-N-(2-hydroxy-(R)-1-phenylethyl)propanoic amide수율 31%HCID 117615803-(4-benzyloxyphenyl)-(S)-2-ethoxy-N-(2-hydroxy-(R)-1-phenylethyl)propanoic amide수율 37%

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매HCID 8900Heptane용매

실험 절차

EDC (2.03 g; 10.61 mmole), diisopropylethylamine (1.84 ml, 10.61 mmole) and HOBt×H2O (1.43 g; 10.61 mmole) were added to a solution of 3-(4-benzyloxyphenyl)-2-ethoxypropanoic acid (2.92 g, 9.74 mmole) in dry dichloromethane (30 ml) on an ice-bath. After 30 minutes the ice-bath was removed and (R)-phenylglycinol (1.46 g, 10.61 mmole) was added. After stirring at room temperature overnight ethyl acetate (100 ml) was added and the solution 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:heptane 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 solution 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-74d42c49009f43ca971d28f2a32b1c50
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06362360B1

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