Hydrochloric Acid → HCID 22176330, compound

HRID 1797745Notes

Reaction equation

HRID 1797745 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][CH2:8][C:9]1[N:10]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:11](=[O:27])[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]([CH2:25][OH:26])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42].Cl>C1(C)C=CC=CC=1.CN(C)CCN(C)C.O1CCCC1>[CH3:40][S:41]([O:26][CH2:25][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:27])[N:10]([CH2:28][CH:29]([CH3:30])[CH3:31])[C:9]([CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:32])=[C:18]2[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)(=[O:43])=[O:42]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22175460HCID 22175460, compound

Product 1

HCID 22176330HCID 22176330, compoundYield 101%

Reagents, catalysts & solvents 3

HCID 8037N,N,N',N'-TetramethylethylenediamineCatalystHCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tert-butyl[6-(hydroxymethyl)-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.33 g, 0.75 mmol), triethylamine (0.18 mL, 1.1 mmol), N,N,N′,N′-tetramethyletylenediamine (0.011 mL, 0.075 mmol), toluene (6 mL) and tetrahydrofuran (6 mL) was added dropwise a solution of methanesulfonyl chloride (0.088 mL, 1.1 mmol) in toluene, (4 mL) under ice-cooling. The mixture was stirred under ice-cooling for 30 min, the reaction mixture was poured into 0.1N hydrochloric acid (50 mL) and extracted with ethyl acetate (50 mL). The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give (3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-6-yl)methyl methanesulfonate (0.39 g, 100%) as colorless powder.

Workup

  1. temperaturecooling
  2. temperaturecooling for 30 min
  3. extractionextracted with ethyl acetate (50 mL)
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ea661bc6b9c740ff919d210a00eb1d79
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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