Triphenylphosphine → [[1-[4-(Aminosulfonyl)phenyl]-5-(4-chlorophenyl)-1h-pyrazol-3-yl]methyl]-n,o-bis(phenoxycarbonyl)hydroxylamine

HRID 1057789

反応式

HRID 1057789 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([CH2:23]O)[CH:9]=2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:44]([C:51]([NH:53][O:54][C:55]([O:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)=[O:56])=[O:52])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[NH2:22][S:19]([C:16]1[CH:15]=[CH:14][C:13]([N:12]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[CH:9][C:10]([CH2:23][N:53]([C:51]([O:44][C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)=[O:52])[O:54][C:55]([O:57][C:58]3[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=3)=[O:56])=[N:11]2)=[CH:18][CH:17]=1)(=[O:21])=[O:20]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 9947165HCID 9947165、化合物HCID 10107329N,O-Bis-(phenoxycarbonyl)-hydroxylamine

生成物 1

HCID 12052545[[1-[4-(Aminosulfonyl)phenyl]-5-(4-chlorophenyl)-1h-pyrazol-3-yl]methyl]-n,o-bis(phenoxycarbonyl)hydroxylamine収率 75%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 4-[5-(4-chlorophenyl-3-hydroxymethyl-1H-pyrazol-1-yl]benzenesulfonamide from Step 4 (7.28 g, 0.02 mol), triphenylphosphine (6.29 g, 0.024 mol) and N,O-bis(phenoxycarbonyl)hydroxylamine prepared as described by A. O. Stewart and D. W. Brooks, [J. Org. Chem., 57, 5020-5023 (1992)] (6.01 g, 0.022 mol) in 250 mL of anhydrous tetrahydrofuran (THF) was cooled to 0° C. and treated with diisopropylazodicarboxylate (3.75 g, 0.024 mol) dissolved in 25 mL of THF. The solution was stirred at room temperature for 3 hours, concentrated in vacuo and the residue purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (2:3) to afford 9.30 g, 75% of the protected hydroxylamine as a thick clear oil that was used directly in the next step.

後処理

  1. concentrationconcentrated in vacuo
  2. customthe residue purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (2:3)

出典と根拠

ORDレコード
ord-ea576c61c796488194b10f561cfa89b1
出典データセット
uspto-grants-2003_02
特許番号
US06515014B2

関連ノート

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