Hydrochloric Acid → HCID 86592785, compound

HRID 1827546Notes

Reaction equation

HRID 1827546 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31]C4CCCCO4)[CH:26]=3)[C:16]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:17])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.C(=O)(O)[O-].[Na+]>C(O)C>[OH:31][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=1)[CH2:24][N:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:10][CH:11]=1)[C:16]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86592786Cyclohexanecarboxylic acid [4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-amide

Product 1

HCID 86592785HCID 86592785, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Cyclohexanecarboxylic acid [4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-amide was deprotected by stirring in a 3:1 solution of ethanol:1N HCl at room temperature for 24 hr. Saturated sodium bicarbonate solution was added until basic, and the aqueous solution was washed with methylene chloride. The organic layer was poured onto a silica gel plug and the product was eluted using a solvent gradient (methylene chloride to 10% methanol/methylene chloride) to obtain the title compound. MS 423.2 (M+1)+

Workup

  1. washwas washed with methylene chloride
  2. additionThe organic layer was poured onto a silica gel plug
  3. washthe product was eluted

Sources & evidence

ORD record
ord-be5e184f6122489d8182cbdf0adb16cd
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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