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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
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HRID 220982 반응식
[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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참가 물질

6

반응물 3

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

생성물 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 Ester수율 9%

시약·촉매·용매 2

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-dc17204376964ba797eb248a751a0fd8
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08202858B2

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