Triethylamine → (3-Bromo-2-oxo-piperidin-1-yl)acetic acid benzyl ester

HRID 1374076

反応式

HRID 1374076 の反応式
S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH2:12]([O:19][C:20](=[O:23])[CH2:21][NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.[Br:31][CH:32]([CH2:36][CH2:37][CH2:38]Br)[C:33](Cl)=[O:34].[OH-].[Na+].C(=O)([O-])O.C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[CH2:12]([O:19][C:20](=[O:23])[CH2:21][N:22]1[CH2:38][CH2:37][CH2:36][CH:32]([Br:31])[C:33]1=[O:34])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

7

反応物 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 6451311O-benzylglycine toluene-p-sulphonateHCID 110121401-Butanaminium, N,N,N-tributyl-, carbonic acid (1:1)HCID 1118503241339-29-1

生成物 1

HCID 69484297(3-Bromo-2-oxo-piperidin-1-yl)acetic acid benzyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

67.7 g (0.2 mol) of glycine benzyl ester tosylate and 61.2 ml (0.44 mol) of triethylamine are dissolved in 200 ml of methylene chloride and added in drops at 0° C. to a solution of 55.7 g (0.2 mol) of 2,5-dibromovaleric acid chloride (Okawara et al. Chem. Pharm. Bull. (1982), (30), 1225) in 200 ml of methylene chloride within 45 minutes, and it is stirred for 18 hours at room temperature. The reaction mixture is now added in drops at 0° C. to a solution of 400 ml of aqueous 32% sodium hydroxide and 2 g of tetrabutylammonium hydrogen carbonate (about 15 minutes), and it is stirred for 30 minutes. Then, the phases are separated, and the aqueous phase is extracted three times with 200 ml of dichloromethane each. The organic phases are dried on sodium sulfate, the solution is evaporated to the dry state and chromatographed on silica gel (methylene chloride). The fractions that contain the product are combined and concentrated by evaporation.

後処理

  1. stirringis stirred for 30 minutes
  2. customThen, the phases are separated
  3. extractionthe aqueous phase is extracted three times with 200 ml of dichloromethane each
  4. customThe organic phases are dried on sodium sulfate
  5. customthe solution is evaporated to the dry state
  6. customchromatographed on silica gel (methylene chloride)
  7. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-9da6f88e5c9d425f975ad89bb11f4551
出典データセット
uspto-grants-2007_01
特許番号
US07164016B2

関連ノート

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