Water → HCID 22175953, compound

HRID 1797657Notes

Reaction equation

HRID 1797657 reaction equation
C([O:5][C:6](=[O:33])[NH:7][CH2:8][C:9]1[N:10]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:11](=[O:28])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:16][C:15]([C:25]([NH2:27])=[S:26])=[CH:14][CH:13]=2)(C)(C)C.C(N(CC)CC)C.ClC(O[CH2:45][CH:46]1[C:58]2[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=2[C:52]2[C:47]1=[CH:48][CH:49]=[CH:50][CH:51]=2)=O.O>Cl.C(OCC)(=O)C>[CH:48]1[C:47]2[CH:46]([CH2:45][O:5][C:6](=[O:33])[NH:7][CH2:8][C:9]3[N:10]([CH2:29][CH:30]([CH3:31])[CH3:32])[C:11](=[O:28])[C:12]4[C:17]([C:18]=3[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:16][C:15]([C:25]([NH2:27])=[S:26])=[CH:14][CH:13]=4)[C:58]3[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=3)[C:52]=2[CH:51]=[CH:50][CH:49]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 343679-Fluorenylmethyl chloroformateHCID 86592075HCID 86592075, compound

Product 1

HCID 22175953HCID 22175953, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tert-butyl[6-(aminothiocarbonyl)-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (3.26 g, 7 mmol) was dissolved in a solution of 4N hydrogen chloride in ethyl acetate (20 ml) and the mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated under reduced pressure and the residue was suspended in tetrahydrofuran (20 ml). To the obtained mixture were added triethylamine (2.0 ml, 14 mmol) and 9-fluorenylmethyl chloroformate (2.72 g, 10.5 mmol) and the mixture was stirred with heating at 0° C. for 1 h. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 9H-fluoren-9-ylmethyl[6-(aminocarbothioyl)-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (3.21 g, 78.1%) as an amorphous.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. stirringthe mixture was stirred
  3. temperaturewith heating at 0° C. for 1 h
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2cc6cae65ab840a39cc6f4e70e86664b
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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