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

HRID 1906362ノート

反応式

HRID 1906362 の反応式
[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]

参加物

4

反応物 2

HCID 104275tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamateHCID 178419670HCID 178419670、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-f4e083788e07445a8f43d5813ef6bf9c
出典データセット
uspto-grants-1987_03
特許番号
US04652551

反応ノート

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