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

HRID 480269

Reaktionsgleichung

Reaktionsgleichung von HRID 480269
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21919333Tetrahydrofurane dichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-c8aa473702e94ae9a3d2f401d66fb394
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06649656B1

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