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

HRID 1755158
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HRID 1755158 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-d4446a241adb44eb8a9be1a3de837c63
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09169201B2

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