Sodium Hydroxide → HCID 21043774, compound

HRID 11871Notes

Reaction equation

HRID 11871 reaction equation
C[O:2][C:3](=[O:47])[C@H:4]([C:23](=[O:46])[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][N:31]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=[CH:26][CH:25]=1)[CH2:5][CH2:6][CH2:7][N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[OH-].[Na+]>CO>[C:39]([N:31]([CH2:30][C:27]1[CH:28]=[CH:29][C:24]([C:23]([C@H:4]([CH2:5][CH2:6][CH2:7][N:8]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[C:9]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:10])[C:3]([OH:47])=[O:2])=[O:46])=[CH:25][CH:26]=1)[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1)([O:41][C:42]([CH3:43])([CH3:44])[CH3:45])=[O:40]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69638119(S)-2-(4-(N-Boc-N-(2-picolyl)aminomethyl)benzoyl)-5-(N-Boc-2-picolylamino)valeric acid methyl ester

Product 1

HCID 21043774HCID 21043774, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound obtained in Example 66-3 (8.96 g) was dissolved in methanol (134.4 ml) and 1 N aqueous solution of sodium hydroxide (134.4 ml) was added. The mixture was stirred for 1 day. After confirming completion of the reaction with TLC, the reaction solution was concentrated under reduced pressure. The residue was dissolved in 1N aqueous solution of sodium hydroxide and washed with diisopropyl ether. 1 N hydrochloric acid aqueous solution was added to the resulting water layer to adjust the pH to 2-3. The solution was extracted with ethyl acetate and the organic layer separated was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and dried under vacuum to obtain the title compound (8.04 g) as a light brown solid.

Workup

  1. customcompletion of the reaction with TLC
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 1N aqueous solution of sodium hydroxide
  4. washwashed with diisopropyl ether
  5. addition1 N hydrochloric acid aqueous solution was added to the resulting water layer
  6. extractionThe solution was extracted with ethyl acetate
  7. customthe organic layer separated
  8. dry with materialwas dried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customdried under vacuum

Sources & evidence

ORD record
ord-12f48c0cf7f24a37988025d4c331fd79
Source dataset
uspto-grants-2006_08
Patent number
US07098215B2

Reaction notes

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