tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate → 4-t-Butyloxycarbonylamino-3-hydroxy-6-methyl-1-phenylheptane

HRID 1906362노트

반응식

HRID 1906362 반응식
[C:1]([NH:8][C@H:9]([CH:14]=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:16]([Mg]Br)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOCC>[C:4]([O:3][C:1]([NH:8][CH:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[CH:14]([OH:15])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:2])([CH3:6])([CH3:5])[CH3:7]

참가 물질

4

반응물 2

HCID 104275tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamateHCID 178419670HCID 178419670, 화합물

생성물 1

HCID 138931534-t-Butyloxycarbonylamino-3-hydroxy-6-methyl-1-phenylheptane수율 79.9%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To a rapidly stirred -78° C. solution of Boc-Leucinal (1.50 g, 6.97 mmol) in anhydrous ether (10 ml) was added a -78° C. solution of phenethyl magnesium bromide (7 mmol) in anhydrous ether (40 ml) dropwise over the course of 15 minutes, and 45 minutes later the mixture was acidified. The oragnic phase was separated, washed with brine (2×10 ml) and dried (Na2SO4). Filtration and evaporation provided an oil (1.79 g) which was chromatographed with 150 g of 40 m SiO2 (7/3, hexane/ether) to give the desired compound (0.17 g). Mass spectrum: M+ =321.

후처리

  1. customThe oragnic phase was separated
  2. washwashed with brine (2×10 ml)
  3. dry with materialdried (Na2SO4)
  4. filtrationFiltration and evaporation

출처 및 근거

ORD 기록
ord-f4e083788e07445a8f43d5813ef6bf9c
출처 데이터셋
uspto-grants-1987_03
특허 번호
US04652551

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