Sodium Hydroxide → HCID 70052853, compound

HRID 567860Notes

Reaction equation

HRID 567860 reaction equation
C([O-])=O.[NH4+].C([O:12][C:13](=[O:47])[CH2:14][N:15]1[C:20]([CH3:21])=[C:19](Cl)[N:18]=[C:17]([NH:23][CH2:24][CH2:25][C:26]2[CH:27]=[C:28]([CH:43]=[CH:44][CH:45]=2)[O:29][CH2:30][C@H:31]2[CH2:35][CH2:34][CH2:33][N:32]2[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:16]1=[O:46])C1C=CC=CC=1.[OH-].[Na+]>[Pd].CO.O>[NH3:15].[C:39]([O:38][C:36]([N:32]1[CH2:33][CH2:34][CH2:35][C@@H:31]1[CH2:30][O:29][C:28]1[CH:27]=[C:26]([CH:45]=[CH:44][CH:43]=1)[CH2:25][CH2:24][NH:23][C:17]1[C:16](=[O:46])[N:15]([CH2:14][C:13]([OH:47])=[O:12])[C:20]([CH3:21])=[CH:19][N:18]=1)=[O:37])([CH3:40])([CH3:41])[CH3:42]

Participants

8

Reactant 3

HCID 14798Sodium HydroxideHCID 2723923Ammonium formateHCID 59900521HCID 59900521, compound

Product 2

HCID 222AmmoniaHCID 70052853HCID 70052853, compoundYield 33.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

10% Palladium on charcoal (125 mg) and ammonium formate (515 mg, 8.17 mmol) were added to a solution of tert-butyl (2R)-2-({3-[2-({4-[2-(benzyloxy)-2-oxoethyl]-6-chloro-5-methyl-3-oxo-3,4-dihydro-2-pyrazinyl}amino)ethyl]phenoxy}methyl)-1-pyrrolidinecarboxylate (preparation 135) (500 mg, 0.82 mmol) in methanol (10 ml), and the reaction stirred at room temperature under a nitrogen atmosphere for 18 hrs, followed by a further 24 hrs, at 50° C. The cooled mixture was filtered through Whatman® fibre, and NaOH (327 mg, 8.17 mmol) in water was added to the filtrate. This solution was evaporated under reduced pressure and the residue purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (90:10:1 to 85:15:2) to provide the desired product, (67 mg, 11%).

Workup

  1. waitfollowed by a further 24 hrs, at 50° C
  2. additionwas added to the filtrate
  3. customThis solution was evaporated under reduced pressure
  4. customthe residue purified by column chromatography on silica gel using an elution gradient of dichloromethane

Sources & evidence

ORD record
ord-129f64aa1f4c4839aee9db5e2ad6baff
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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