Sodium Hydroxide → THRX-195518

HRID 252884Notes

Reaction equation

HRID 252884 reaction equation
[OH-].[Na+].C([O:5][C:6]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:48])[N:22]([CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][CH:29]([O:32][C:33](=[O:47])[NH:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[CH2:28][CH2:27]3)[CH3:23])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])C>CO>[C:36]1([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[NH:34][C:33]([O:32][CH:29]1[CH2:30][CH2:31][N:26]([CH2:25][CH2:24][N:22]([CH3:23])[C:21]([C:18]2[CH:19]=[CH:20][C:15]([CH2:14][N:11]3[CH2:10][CH2:9][CH:8]([C:6]([OH:7])=[O:5])[CH2:13][CH2:12]3)=[CH:16][CH:17]=2)=[O:48])[CH2:27][CH2:28]1)=[O:47]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57459432HCID 57459432, compound

Product 1

HCID 57459433THRX-195518Yield 75.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 200 mL flask was added 1N NaOH (40 mL), MeOH (40 mL) and 1-[4-({2-[4-(biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]ethyl}methylcarbamoyl)benzyl]piperidine-4-carboxylic acid ethyl ester (1.12 g, 1.7 mmol; prepared as described in Preparation 6). The reaction was allowed to stir at room temperature for 16 hours. The reaction mixture was then concentrated under reduced pressure and this mixture was acidified with 1N HCl (40 mL) at 0-5° C. with an ice bath. The product was then extracted with DCM (2×50 mL). The combined organic layers were washed with water (100 mL), brine (100 mL), dried over sodium sulfate, filtered and concentrated to afford the title compound (0.80 g, 1.28 mmol) in 75% yield. The title compound was sufficiently pure to use without further purification.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customthis mixture was acidified with 1N HCl (40 mL) at 0-5° C. with an ice bath
  3. extractionThe product was then extracted with DCM (2×50 mL)
  4. washThe combined organic layers were washed with water (100 mL), brine (100 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-83ef493ce1924f0a9a623ccdc8de2c26
Source dataset
uspto-grants-2011_01
Patent number
US07868175B2

Reaction notes

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