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Triethylamine → [2-Methyl-4-(2-methyl-4,5-dihydro-1-oxa-3,6-diaza-benzo[e]azulene-6-carbonyl)-benzyl]-carbamic Acid Tert-butyl Ester

HRID 220982
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 220982
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][C:11]=1[CH3:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:27][C:28]1[O:37][C:36]2[C:35]3[CH:38]=[CH:39][CH:40]=[CH:41][C:34]=3[NH:33][CH2:32][CH2:31][C:30]=2[N:29]=1>ClCCl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([N:33]2[CH2:32][CH2:31][C:30]3[N:29]=[C:28]([CH3:27])[O:37][C:36]=3[C:35]3[CH:38]=[CH:39][CH:40]=[CH:41][C:34]2=3)=[O:16])=[CH:12][C:11]=1[CH3:19])([CH3:2])([CH3:3])[CH3:4]
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Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 231123652-methyl-5,6-dihydro-4H-benzo[b]oxazolo[5,4-d]azepineHCID 575554314-((Tert-butoxycarbonylamino)methyl)-3-methylbenzoic acid

Produkt 1

HCID 57555363[2-Methyl-4-(2-methyl-4,5-dihydro-1-oxa-3,6-diaza-benzo[e]azulene-6-carbonyl)-benzyl]-carbamic Acid Tert-butyl EsterAusbeute 9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4-(tert-butoxycarbonylamino-methyl)-3-methyl-benzoic acid from Example E2h (400 mg, 1.5 mmol) in dichloromethane (20 ml) and triethylamine (to pH9) was treated with WSCD (573 mg, 3.0 mmol) and DMAP (183 mg, 1.5 mmol). The solution was stirred for 30 min at room temperature then 2-methyl-5,6-dihydro-4H-1-oxa-3,6-diaza-benzo[e]azulene from Example E6 (300 mg, 1.5 mmol) was added and the mixture was heated at reflux for 3 days. WSCD (287 mg, 1.5 mmol) was added and the mixture was heated at reflux for another 24h then concentrated in vacuo. The residue was dissolved in EtOAc, washed with 1N KHSO4, water then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; EtOAc) to yield the title compound (62 mg, 9%).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 days
  3. additionWSCD (287 mg, 1.5 mmol) was added
  4. temperaturethe mixture was heated
  5. concentrationthen concentrated in vacuo
  6. dissolutionThe residue was dissolved in EtOAc
  7. washwashed with 1N KHSO4, water
  8. dry with materialbrine, dried
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash chromatography on silica gel (eluant; EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-dc17204376964ba797eb248a751a0fd8
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08202858B2

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