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

HRID 1374076

반응식

HRID 1374076 반응식
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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9da6f88e5c9d425f975ad89bb11f4551
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07164016B2

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