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HCID 69075315, 화합물 → (3-{(S)-1-[(R)-1-(3-Benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propyl]-2-p-tolyl-4,5-dihydro-1H-imidazol-4-yl}-propyl)-carbamic acid benzyl ester

HRID 1350638
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HRID 1350638 반응식
C(OC(=O)[NH:7][CH:8]([CH2:23][N:24]([CH:34]([C:38]1[N:47]([CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:46](=[O:55])[C:45]2[C:40](=[CH:41][C:42]([Cl:56])=[CH:43][CH:44]=2)[N:39]=1)[CH:35]([CH3:37])[CH3:36])[C:25]([C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=1)=O)[CH2:9][CH2:10][CH2:11][NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH2:16]([O:15][C:13](=[O:14])[NH:12][CH2:11][CH2:10][CH2:9][C@H:8]1[CH2:23][N:24]([C@@H:34]([C:38]2[N:47]([CH2:48][C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)[C:46](=[O:55])[C:45]3[C:40](=[CH:41][C:42]([Cl:56])=[CH:43][CH:44]=3)[N:39]=2)[CH:35]([CH3:37])[CH3:36])[C:25]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)=[N:7]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
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참가 물질

3

반응물 1

HCID 69075315HCID 69075315, 화합물

생성물 1

HCID 58861274(3-{(S)-1-[(R)-1-(3-Benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propyl]-2-p-tolyl-4,5-dihydro-1H-imidazol-4-yl}-propyl)-carbamic acid benzyl ester수율 40%

시약·촉매·용매 1

HCID 21863450Trifluoroacetic acid methylene chloride용매

실험 절차

A solution of (1-{[[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propyl]-(1-p-tolyl-methanoyl)-amino]-methyl}-4-benzyloxycarbonylamino-butyl)-carbamic acid tert-butyl ester (235 mg, 0.37 mmol) in CH2Cl2/TFA (4:1, 5 mL) was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the residue was diluted with CH2Cl2 (10 mL) and washed with saturated aqueous NaHCO3 (10 mL). The aqueous layer was extracted with CH2Cl2 and the combined extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was diluted with THF (10 mL) and saturated aqueous NaHCO3 (1 mL). The mixture was stirred at room temperature for 10 days, diluted with ether (20 mL) and washed with brine. The aqueous layer was extracted with two 10 mL portions of EtOAc and the combined extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (19:1 CH2Cl2:MeOH) to provide 81 mg (40%) of the title compound as a pale white powder. MS(ES+) m/e 675.6 [M+H]+.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with CH2Cl2 (10 mL)
  3. washwashed with saturated aqueous NaHCO3 (10 mL)
  4. extractionThe aqueous layer was extracted with CH2Cl2
  5. dry with materialthe combined extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. additionThe residue was diluted with THF (10 mL) and saturated aqueous NaHCO3 (1 mL)
  9. additiondiluted with ether (20 mL)
  10. washwashed with brine
  11. extractionThe aqueous layer was extracted with two 10 mL portions of EtOAc
  12. dry with materialthe combined extracts were dried over MgSO4
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure
  15. customThe residue was purified by silica gel chromatography (19:1 CH2Cl2:MeOH)

출처 및 근거

ORD 기록
ord-c70509933e7f44a2967d55d1008a85db
출처 데이터셋
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07214800B2

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