Hydrochloric Acid → HCID 68196368, compound

HRID 1626798Notes

Reaction equation

HRID 1626798 reaction equation
C(C([NH:12][C:13]([C:15]1[C:20]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:19]([CH3:29])[N:18]=[C:17]([CH2:30][CH:31]2[CH2:36][CH2:35][N:34]([C:37]3[CH:42]=[CH:41][C:40]([C:43]4[CH:48]=[CH:47][C:46]([CH:49]([O:51]COC)[CH3:50])=[CH:45][N:44]=4)=[CH:39][CH:38]=3)[CH2:33][CH2:32]2)[N:16]=1)=[O:14])C([O-])=O)C1C=CC=CC=1.Cl.O1CCOCC1.[CH3:62][CH2:63][CH2:64][CH2:65][CH2:66]C.[C:68]([O:71][CH2:72][CH3:73])(=[O:70])[CH3:69]>>[CH2:22]([O:21][C:20]1[C:15]([C:13]([NH:12][CH2:69][C:68]([O:71][CH2:72][C:73]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)=[O:70])=[O:14])=[N:16][C:17]([CH2:30][CH:31]2[CH2:36][CH2:35][N:34]([C:37]3[CH:42]=[CH:41][C:40]([C:43]4[CH:48]=[CH:47][C:46]([CH:49]([OH:51])[CH3:50])=[CH:45][N:44]=4)=[CH:39][CH:38]=3)[CH2:33][CH2:32]2)=[N:18][C:19]=1[CH3:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 8857Ethyl AcetateHCID 312751,4-DioxaneHCID 86670084HCID 86670084, compound

Product 1

HCID 68196368HCID 68196368, compoundYield 44%

Procedure

Benzyl({[5-(benzyloxy)-2-{[1-(4-{5-[1-(methoxymethoxy)ethyl]pyridin-2-yl}phenyl)piperidin-4-yl]methyl}-6-methylpyrimidin-4-yl]carbonyl}amino)acetate (0.80 g, 1.1 mmol) was dissolved in ethyl acetate (6 mL), and a solution of hydrogen chloride in dioxane (4 M, 1.5 mL, 6.0 mmol) was added, followed by stirring at room temperature for 1.5 hours. After hexane was added to the reaction solution, the deposited solid was collected by filtration using hexane. To this, was added a saturated aqueous sodium hydrogencarbonate solution, followed by extraction with ethyl acetate, and subsequently the organic layer was concentrated under reduced pressure. The resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.30 (hexane/ethyl acetate=1/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (0.32 g, 0.49 mmol) as a yellow solid (yield 44%).

Workup

  1. filtrationthe deposited solid was collected by filtration
  2. additionTo this, was added a saturated aqueous sodium hydrogencarbonate solution
  3. extractionfollowed by extraction with ethyl acetate
  4. concentrationsubsequently the organic layer was concentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  6. concentrationa fraction corresponding to the Rf value=0.30 (hexane/ethyl acetate=1/1) by thin layer chromatography was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c6a7ef3c5ba04a24aa0d508a3ce32095
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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