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4-Hydroxybenzoic Acid → Tert-butyl 4-{4-[(4-hydroxybenzoyl)amino]phenyl}piperazine-1-carboxylate

HRID 906046
ノート
印刷プレビュー

反応式

HRID 906046 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=1.CN1CCOCC1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[OH:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)=[O:27])=[CH:24][CH:23]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 1354-Hydroxybenzoic AcidHCID 79724-MethylmorpholineHCID 2724699PyBOPHCID 11011301tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylate

生成物 1

HCID 54019812Tert-butyl 4-{4-[(4-hydroxybenzoyl)amino]phenyl}piperazine-1-carboxylate収率 24%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
60 °C

実験手順

To a solution of tert-butyl 4-(4-aminophenyl)piperazine-1-carboxylate (1 eq), 4-hydroxybenzoic acid (1.1 eq), N-methylmorpholine (3 eq) in dry DMF (0.16 M), was added PyBop (1.5 eq). The reaction mixture was heated at 60° C. with stirring for 60 h. At this time the reaction was allowed to cool to RT partitioned between EtOAc and 1N aqueous HCl. The aqueous fraction was extracted with EtOAc and the combined organics washed with saturated aqueous Na2CO3, brine, before being dried over Na2SO4, filtered and evaporated in vacuo. Purification was by flash chromatography on silica gel (4:6) EtOAc/PE) to afford the title compound (24%).

後処理

  1. temperatureto cool to RT
  2. custompartitioned between EtOAc and 1N aqueous HCl
  3. extractionThe aqueous fraction was extracted with EtOAc
  4. washthe combined organics washed with saturated aqueous Na2CO3, brine
  5. dry with materialbefore being dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customPurification

出典と根拠

ORDレコード
ord-d98d7e3d44304e96852ff05aaa8aa53a
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08012982B2

反応ノート

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