Hydrochloric Acid → HCID 58909227, compound

HRID 1985092Notes

Reaction equation

HRID 1985092 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[C:33]([F:35])[CH:34]=1)[CH2:5][C@H:6]([NH:24]C(=O)OC(C)(C)C)[C@H:7]([OH:23])[CH2:8][NH:9][CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH3:21])[CH:18]=2)[N:13]([CH3:22])[CH2:12][CH2:11]1.Cl>CO.CCOCC>[NH2:24][C@@H:6]([CH2:5][C:4]1[CH:3]=[C:2]([F:1])[CH:34]=[C:33]([F:35])[CH:32]=1)[C@H:7]([OH:23])[CH2:8][NH:9][CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH3:21])[CH:18]=2)[N:13]([CH3:22])[CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58909284HCID 58909284, compound

Product 1

HCID 58909227HCID 58909227, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of tert-butyl (1S,2R)-1-(3,5-difluorobenzyl)-3-[(6-ethyl-1-methyl-1,2,3,4-tetrahydroquinolin-4-yl)amino]-2-hydroxypropylcarbamate (0.412 g) in MeOH (5 mL) was added 2N HCl in Et2O (2.1 mL). The mixture was stirred at room temperature for fifteen minutes. The mixture was stripped of solvent under reduced pressure. The residue was partitioned between dichloromethane and aqueous sodium bicarbonate, and the organic was extracted three times, washed with brine, dried with sodium sulfate, filtered, and concentrated. A silica gel column was run for purification using 5% MeOH in dichloromethane with as the solvent solution. 0.255 g of the title product were recovered. (78% yield). MS (ESI+) for C22H29F2N3O m/z 390.18 (M+H)+.

Workup

  1. customThe residue was partitioned between dichloromethane and aqueous sodium bicarbonate
  2. extractionthe organic was extracted three times
  3. washwashed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customA silica gel column was run for purification
  8. custom0.255 g of the title product were recovered

Sources & evidence

ORD record
ord-53665358f76f4f34abf1db61fa9dbd0c
Source dataset
uspto-grants-2009_06
Patent number
US07544717B2

Reaction notes

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