N,N,N',N'-Tetramethylazodicarboxamide → 2-(2-(4-(4-(3-(tert-butoxycarbonylamino)benzyloxy)phenoxy)-phenyl)acetylamino)benzoic Acid Methyl Ester

HRID 480269

반응식

HRID 480269 반응식
[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:27])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[CH:15][CH:14]=1.[C:29]([O:33][C:34]([NH:36][C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][CH:44]=1)[CH2:40]O)=[O:35])([CH3:32])([CH3:31])[CH3:30].N(C(N(C)C)=O)=NC(N(C)C)=O.C(P(CCCC)CCCC)CCC>C(Cl)Cl.C1COCC1>[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:27])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][CH2:40][C:39]3[CH:42]=[CH:43][CH:44]=[C:37]([NH:36][C:34]([O:33][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:35])[CH:38]=3)=[CH:24][CH:25]=2)=[CH:15][CH:14]=1

참가 물질

6

반응물 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 14523557tert-Butyl (3-(hydroxymethyl)phenyl)carbamateHCID 20602792Methyl 2-(4-(4-hydroxyphenoxy)phenylacetamido)benzoate

생성물 1

HCID 206027912-(2-(4-(4-(3-(tert-butoxycarbonylamino)benzyloxy)phenoxy)-phenyl)acetylamino)benzoic Acid Methyl Ester수율 83%

시약·촉매·용매 1

HCID 21919333Tetrahydrofurane dichloromethane용매

실험 절차

2-(2-(4-(4-Hydroxyphenoxy)phenyl)acetylamino)benzoic acid methyl ester obtained by the Reference Example 24 (315 mg, 0.83 mmol) was dissolved in 20 ml of methylene chloride-THF mixture (1:1 v/v), added with 3-(tert-butoxycarbonylamino)benzyl alcohol (465 mg, 2.1 mmol), 1,1′-azobis(N,N′-dimethylformamide) (359 mg, 2.08 mmol) and tri-n-butyl phosphine (520 ml, 2.1 mmol) and the reaction mixture was stirred over a night. After completing the reaction, the solvent was removed under reduced pressure and the obtained crude residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate 75:25 v/v) to obtain the subject compound (404 mg, 0.693 mmol) in the form of a colorless gummy substance. The result of 1H-NMR was consistent with the above structure.

후처리

  1. customthe reaction
  2. customthe solvent was removed under reduced pressure
  3. customthe obtained crude residue
  4. customwas purified by silica gel chromatography (elution solvent; hexane:ethyl acetate 75:25 v/v)

출처 및 근거

ORD 기록
ord-c8aa473702e94ae9a3d2f401d66fb394
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06649656B1

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