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4-Iodoaniline → 4-{[(4-tert-Butyl-phenyl)-(4-iodo-phenylcarbamoyl)-methyl]-amino}-benzoic Acid Tert-butyl Ester

HRID 1755158
ノート
印刷プレビュー

反応式

HRID 1755158 の反応式
[C:1]([O:5][C:6](=[O:28])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH:14]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:20][CH:19]=2)[C:15]([OH:17])=O)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.[I:39][C:40]1[CH:46]=[CH:45][C:43]([NH2:44])=[CH:42][CH:41]=1.CCN(C(C)C)C(C)C>CN(C=O)C.O.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:28])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH:14]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([CH3:25])([CH3:27])[CH3:26])=[CH:20][CH:19]=2)[C:15](=[O:17])[NH:44][C:43]2[CH:45]=[CH:46][C:40]([I:39])=[CH:41][CH:42]=2)=[CH:9][CH:8]=1)([CH3:3])([CH3:4])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 108934-IodoanilineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 674862324-{[(4-tert-Butyl-phenyl)-carboxy-methyl]-amino}-benzoic Acid Tert-butyl Ester

生成物 1

HCID 674865594-{[(4-tert-Butyl-phenyl)-(4-iodo-phenylcarbamoyl)-methyl]-amino}-benzoic Acid Tert-butyl Ester収率 70%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(4-{[(4-tert-Butyl-phenyl)-carb oxy-methyl]-amino}-benzoic acid tert-butyl ester (760 mg, 2.0 mmol), was taken up in 5 mL of DMF followed by addition of HOBt (765 mg, 5.0 mmol) and EDCT (958 mg, 5.0 mmol). The reaction was stirred at RT for 30 min, 4-iodoaniline (657 mg, 3 mmol) was added followed by Hunig's base (640 mg, 5 mmol) and allowed to stir an additional 16 h at RT. Ethyl acetate (20 mL) and 20 mL water were added and separated. The aqueous layer was then back extracted with another 10 mL of EtOAc, the organic layer were combined and washed with water (3×20 mL). The organic layer was dried over sodium sulfate, filtered and the solvent was removed under reduced pressure to give a brown solid. The solids were triturated with methanol to give a white solid (818 mg, 70%). 1H NMR (CDCl3): δ 1.32 (9H, s), 1.58 (9H, s), 4.89 (2H, d), 5.02 (1H, d), 6.62 (2H, d, J=8.4 Hz), 7.22-7.95 (10H, m), 8.81 (1H, s).

後処理

  1. stirringto stir an additional 16 h at RT
  2. customseparated
  3. extractionThe aqueous layer was then back extracted with another 10 mL of EtOAc
  4. washwashed with water (3×20 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customto give a brown solid
  9. customThe solids were triturated with methanol

出典と根拠

ORDレコード
ord-d4446a241adb44eb8a9be1a3de837c63
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09169201B2

反応ノート

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