Acetone → 2-Dibenzylamino-3-hydroxy-3-methyl-butyric acid ethyl ester

HRID 1348638

반응식

HRID 1348638 반응식
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][N:6]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].C([N-]C(C)C)(C)C.[Li+].[CH3:30][C:31]([CH3:33])=[O:32].[Cl-].[NH4+]>O1CCCC1.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:21])[CH:5]([N:6]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:31]([OH:32])([CH3:33])[CH3:30])[CH3:2]

참가 물질

7

반응물 4

HCID 180AcetoneHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 3553452Ethyl 2-(dibenzylamino)acetate

생성물 1

HCID 148244862-Dibenzylamino-3-hydroxy-3-methyl-butyric acid ethyl ester수율 52.4%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 11.3 g (40.0 mmol) dibenzylamino-acetic acid ethyl ester in 107 ml tetrahydrofuran and 107 ml toluene was stirred at −70° C. with 22 ml (44 mmol) lithium diisopropylamide (2M in heptane) for 30 minutes. 3.40 ml (46 mmol) acetone were added and stirring was continued overnight. The mixture was allowed to warm to room temprature, aqueous ammonium chloride solution was added. Extraction with diethylether and chromatography on silicagel with diethylether/heptane 1/2 yielded 7.16 g (52%) 2-dibenzylamino-3-hydroxy-3-methyl-butyric acid ethyl ester, MS m/e (%): 342.3 (M+H+, 100).

후처리

  1. additionwas added
  2. extractionExtraction with diethylether and chromatography on silicagel with diethylether/heptane 1/2

출처 및 근거

ORD 기록
ord-c0e1b14399da4007b17d1580dce6c4c8
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07211573B2

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