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

HRID 279683ノート

反応式

HRID 279683 の反応式
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

参加物

11

反応物 6

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

生成物 2

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

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒HCID 8900Heptane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-74d42c49009f43ca971d28f2a32b1c50
出典データセット
uspto-grants-2002_03
特許番号
US06362360B1

反応ノート

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