Triphenylphosphine → 4-methoxybenzyl N-[4-bromo-1-(tert-butoxycarbonyl)-1H-pyrazol-3-yl]-N-[(2,2,2-trichloroethoxy)carbonyl]leucinate

HRID 1744130

反応式

HRID 1744130 の反応式
[Br:1][C:2]1[C:3]([NH:14][C:15]([O:17][CH2:18][C:19]([Cl:22])([Cl:21])[Cl:20])=[O:16])=[N:4][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH:6]=1.O[CH:24]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)=[O:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>CN(C=O)C.O>[Br:1][C:2]1[C:3]([N:14]([C:15]([O:17][CH2:18][C:19]([Cl:20])([Cl:22])[Cl:21])=[O:16])[C@H:24]([C:25]([O:27][CH2:28][C:29]2[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=2)=[O:26])[CH2:37][CH:38]([CH3:40])[CH3:39])=[N:4][N:5]([C:7]([O:9][C:10]([CH3:12])([CH3:13])[CH3:11])=[O:8])[CH:6]=1

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 22235916HCID 22235916、化合物HCID 222360714-Methoxybenzyl 2-hydroxy-4-methylpentanoate

生成物 1

HCID 691522654-methoxybenzyl N-[4-bromo-1-(tert-butoxycarbonyl)-1H-pyrazol-3-yl]-N-[(2,2,2-trichloroethoxy)carbonyl]leucinate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To tert-butyl 4-bromo-3-{[(2,2,2-trichloroethoxy)carbonyl]amino}-1H-pyrazole-1-carboxylate (2.32 g, 5.3 mmol), 4-methoxybenzyl 2-hydroxy-4-methylpentanoate (2.02 g, 8.0 mmol, prepared as described in Example 16) and triphenyl phosphine (2.1 g, 8.0 mmol) in dry DMF (50 mL) at 0° C. under dry nitrogen was added diisopropyl azodicarboxylate (1.6 mL, 8.0 mmol) dropwise and the reaction was stirred overnight. The reaction was poured into water and the product extracted with Et2O (2×), dried over Na2SO4, concentrated in vacuo and purified by flash chromatography over silica gel (EtOAc/Hex, 2/8) to afford 4-methoxybenzyl N-[4-bromo-1-(tert-butoxycarbonyl)-1H-pyrazol-3-yl]—N-[(2,2,2-trichloroethoxy)carbonyl]leucinate.

後処理

  1. extractionthe product extracted with Et2O (2×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography over silica gel (EtOAc/Hex, 2/8)

出典と根拠

ORDレコード
ord-701385ae05034063819110b4904b4ec0
出典データセット
uspto-grants-2006_03
特許番号
US07012075B2

関連ノート

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