Hydrochloric Acid → HCID 67205065, compound

HRID 2041735Notes

Reaction equation

HRID 2041735 reaction equation
CC([N:5]([C@H:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]#[C:20][Si:21]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])[CH:17]=2)[N:12]([C:31](=[O:33])[CH3:32])[C@@H:11]([CH3:34])[CH2:10]1)C(=O)[O-])(C)C.[ClH:35]>O1CCOCC1>[ClH:35].[C:31]([N:12]1[C:13]2[C:18](=[CH:17][C:16]([C:19]#[C:20][Si:21]([CH:22]([CH3:24])[CH3:23])([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])=[CH:15][CH:14]=2)[C@H:9]([NH2:5])[CH2:10][C@@H:11]1[CH3:34])(=[O:33])[CH3:32]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86669451HCID 86669451, compound

Product 1

HCID 67205065HCID 67205065, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1,1-dimethylethyl((2S,4R)-1-acetyl-2-methyl-6-{[tris(1-methylethyl)silyl]ethynyl}-1,2,3,4-tetrahydro-4-quinolinyl)carbamate (for a preparation see Intermediate 107) (1.96 g, 4.04 mmol) in 1,4-dioxane (10 mL) at room temperature was treated with HCl (4N in dioxane, 20 mL, 80 mmol) and the resulting mixture was stirred at this temperature for 7 h then the solvent was removed in vacuo. The residue was triturated with Et2O then filtered off and dried under house vacuum to give (2S,4R)-1-acetyl-2-methyl-6-{[tris(1-methylethyl)silyl]ethynyl}-1,2,3,4-tetrahydro-4-quinolinamine hydrochloride (1.28 g, 3.04 mmol, 75% yield) as a white solid. The mother liquors were concentrated in vacuo to give (2S,4R)-1-acetyl-2-methyl-6-{[tris(1-methylethyl)silyl]ethynyl}-1,2,3,4-tetrahydro-4-quinolinamine hydrochloride (396 mg, 0.940 mmol, 23.26% yield) as a very pale yellow foam.

Workup

  1. customat room temperature
  2. customthe solvent was removed in vacuo
  3. customThe residue was triturated with Et2O
  4. filtrationthen filtered off
  5. customdried under house vacuum

Sources & evidence

ORD record
ord-f10e76c1db894d11b54e3aefe1e87da6
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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