3-(Trifluoromethyl)phenol → HCID 21921562、化合物

HRID 1245097ノート

反応式

HRID 1245097 の反応式
FC1C=C[C:5]([C:6]([OH:8])=[O:7])=CC=1[N+]([O-])=O.F[C:15](F)(F)[C:16]1[CH:17]=[C:18](O)[CH:19]=[CH:20][CH:21]=1.[N+:25]([C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][C:36]=1[O:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:47])([F:46])[F:45])[CH:39]=1)[C:31]([OH:33])=[O:32])([O-:27])=[O:26].CC(C)[N:50]=C=NC(C)C.[CH:57]1[CH:58]=[CH:59][C:60]2N(O)N=N[C:61]=2[CH:62]=1>CN(C=O)C.CN(C1C=CN=CC=1)C>[N+:25]([C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][C:36]=1[O:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:45])([F:46])[F:47])[CH:39]=1)[C:31]([OH:33])=[O:32])([O-:27])=[O:26].[C:19]1([C:62]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH:18]=[CH:17][C:16]([CH2:15][C@H:5]([NH:50][C:31](=[O:32])[C:30]2[CH:34]=[CH:35][C:36]([O:37][C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:47])([F:46])[F:45])[CH:39]=3)=[C:28]([N+:25]([O-:27])=[O:26])[CH:29]=2)[C:6]([OH:8])=[O:7])=[CH:21][CH:20]=1

参加物

9

反応物 5

HCID 73763-(Trifluoromethyl)phenolHCID 12734DiisopropylcarbodiimideHCID 679874-Fluoro-3-nitrobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 21921562HCID 21921562、化合物

生成物 2

HCID 21921562HCID 21921562、化合物収率 81%HCID 58717697HCID 58717697、化合物収率 79%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒2 回

実験手順

3-Nitro-4-(3-trifluoromethyl-phenoxy)-benzoic acid (530 mg, 81%) was prepared from 4-fluoro-3-nitro-benzoic acid (370 mg, 2.0 mmol) and 3-trifluoromethyl phenol (324 mg, 2.0 mmol) as in general procedure B. To Wang resin (60 mg, 0.06 mmol, 1.1 mmol/g) loaded with 4-L-biphenylalanine were added 82 mg of (0.25 mmol) 3-nitro-4-(3-trifluoromethyl-phenoxy)-benzoic acid (82 mg, 0.25 mmol), 1.0 M DIC (1.5 mL, 1.5 mmol) in DMF, 1.0 M HOBt (1.5 mL, 1.5 mmol) in DMF, and a catalytic amount of DMAP. The resulting mixture was left on shaker overnight. The resin was washed with DMF, MeOH, DCM three times of each and cleaved with 20% TFA in DCM. The residue obtained after removing the solvent was purified by chromatography to give the title compound (26 mg, 79%).

後処理

  1. washThe resin was washed with DMF, MeOH, DCM three times of each and
  2. customThe residue obtained
  3. customafter removing the solvent
  4. customwas purified by chromatography

出典と根拠

ORDレコード
ord-db2cf75198264026bf372f0770fc85e4
出典データセット
uspto-grants-2006_10
特許番号
US07122580B2

反応ノート

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