HOAt → (R)-{2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionyl}-pyrrolidine-2-carboxylic acid ethyl ester

HRID 1994078

反応式

HRID 1994078 の反応式
Cl.[CH2:2]([O:4][C:5]([C@H:7]1[CH2:11][CH2:10][CH2:9][NH:8]1)=[O:6])[CH3:3].[CH3:12][C:13]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][C:26]2[N:27]=[C:28]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[O:29][C:30]=2[CH3:31])[CH:19]=1)([CH3:17])[C:14](O)=[O:15].CCN=C=NCCCN(C)C.Cl.ON1C2N=CC=CC=2N=N1>C(Cl)Cl.C(OCC)(=O)C>[CH2:2]([O:4][C:5]([C@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:14](=[O:15])[C:13]([CH3:12])([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][C:26]2[N:27]=[C:28]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[O:29][C:30]=2[CH3:31])[CH:19]=1)[CH3:17])=[O:6])[CH3:3]

参加物

7

反応物 4

HCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 56777374H-D-Pro-oet hclHCID 686756732-Methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionic acid

生成物 1

HCID 68675740(R)-{2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionyl}-pyrrolidine-2-carboxylic acid ethyl ester

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of (R)-pyrrolidine-2-carboxylic acid ethyl ester hydrochloride (1.7 g, 9.4 mmot), TEA (1.0 g, 10.3 mmol) and the title C compound, 2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionic acid (3.0 g, 8.55 mmol) in DCM (50 mL) is added EDCl (2.0 g, 10.3 mmol) and 1-hydroxy-7-azabenzotriazole (HOAt, 1.2 g, 8.55 mmol) at RT. The reaction mixture is stirred for 48 h. The reaction mixture is diluted with ethyl acetate, washed with 2 N aqueous HCl, water, 2 N aqueous sodium hydroxide, water and brine, dried over anhydrous magnesium sulfate and concentrated at reduced pressure. The crude product is purified on a Biotage 40M column using 35% ethyl acetate in hexane to yield (R)-1-{2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionyl}-pyrrolidine-2-carboxylic acid ethyl ester as a clear oil.

後処理

  1. washwashed with 2 N aqueous HCl, water, 2 N aqueous sodium hydroxide, water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated at reduced pressure
  4. customThe crude product is purified on a Biotage 40M column

出典と根拠

ORDレコード
ord-3a2b8c67ab0e4053aa57fce765fe600f
出典データセット
uspto-grants-2010_01
特許番号
US07652061B2

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