Hydrochloric Acid → HCID 66906175, compound

HRID 1691728Notes

Reaction equation

HRID 1691728 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26]2[C:36]([Cl:37])=[CH:35][C:29]([C:30]([O:32]CC)=[O:31])=[CH:28][N:27]=2)[CH2:22][CH:21]1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C@@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[OH-].[Na+].Cl>CO>[C:1]([O:5][C:6]([N:8]([CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26]2[C:36]([Cl:37])=[CH:35][C:29]([C:30]([OH:32])=[O:31])=[CH:28][N:27]=2)[CH2:22][CH:21]1[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C@@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)[CH3:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66906099HCID 66906099, compound

Product 1

HCID 66906175HCID 66906175, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 131 mg of ethyl 6-[4-({(tert-butoxycarbonyl)[(1R)-1-(3-methoxyphenyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]-5-chloronicotinate were added 2.0 mL of THF, 1.0 mL of methanol, and 1.0 mL of a 1 M aqueous sodium hydroxide solution, followed by stirring at room temperature for 2 days. It was neutralized by addition of 1.1 mL of 1 M hydrochloric acid, and then extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and dried to obtain 143 mg of a colorless foamy substance of 6-[4-({(tert-butoxycarbonyl)[(1R)-1-(3-methoxyphenyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]-5-chloronicotinic acid as a crude product. ESI+: 580

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customdried

Sources & evidence

ORD record
ord-0576f94c03d244bfab4d8fc73419685d
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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